WO2021013799A1 - Substituted n-phenyl uracils, salts thereof and their use as herbicidal agents - Google Patents

Substituted n-phenyl uracils, salts thereof and their use as herbicidal agents Download PDF

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Publication number
WO2021013799A1
WO2021013799A1 PCT/EP2020/070463 EP2020070463W WO2021013799A1 WO 2021013799 A1 WO2021013799 A1 WO 2021013799A1 EP 2020070463 W EP2020070463 W EP 2020070463W WO 2021013799 A1 WO2021013799 A1 WO 2021013799A1
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WIPO (PCT)
Prior art keywords
alkyl
alkoxy
aryl
ene
cio
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PCT/EP2020/070463
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German (de)
French (fr)
Inventor
Ines Heinemann
Jens Frackenpohl
Lothar Willms
Harald Jakobi
Hendrik Helmke
Christopher Hugh Rosinger
Elmar Gatzweiler
Elisabeth ASMUS
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Bayer Aktiengesellschaft
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to US17/628,524 priority Critical patent/US20220289708A1/en
Priority to JP2022504186A priority patent/JP2022542068A/en
Priority to AU2020318681A priority patent/AU2020318681A1/en
Priority to EP20743136.2A priority patent/EP4003981A1/en
Priority to MX2022000911A priority patent/MX2022000911A/en
Priority to BR112021026526A priority patent/BR112021026526A2/en
Priority to CA3147953A priority patent/CA3147953A1/en
Priority to CN202080061973.XA priority patent/CN114401956A/en
Priority to KR1020227005304A priority patent/KR20220035935A/en
Publication of WO2021013799A1 publication Critical patent/WO2021013799A1/en

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Definitions

  • the invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and grass weeds in crops of useful plants.
  • This invention specifically relates to substituted N-phenyluracils and their salts, processes for their preparation and their use as herbicides, in particular for controlling weeds and / or grass weeds in crops of useful plants and / or as plant growth regulators for influencing the growth of crops of useful plants.
  • Crops of useful plants or active ingredients for controlling unwanted vegetation sometimes have disadvantages when they are used, be it that they (a) have no or inadequate herbicidal activity against certain harmful plants, (b) an insufficient spectrum of harmful plants that can be controlled with an active ingredient can be, (c) too low selectivity in crops of useful plants and / or (d) have a toxicologically unfavorable profile.
  • some active ingredients which can be used as plant growth regulators in some useful plants lead to undesirably reduced yields in other useful plants or are incompatible with the cultivated plant, or only compatible with a narrow application rate range.
  • Some of the known active ingredients cannot be produced economically on an industrial scale because of the difficult accessibility of precursors and reagents, or they have insufficient chemical stabilities. With other active ingredients, the effect depends too much on environmental conditions, such as weather and soil conditions.
  • N-phenyluracils with optionally further substituted lactic acid groups can also be used as herbicidal active ingredients (cf. JP2000 / 302764, JP2001 / 172265, US6403534, EP408382). It is also known that N-phenyluracils with special, optionally further substituted thiolactic acid groups also show herbicidal effects (cf. WO2010 / 038953, KR2011110420). Special substituted tetrahydrofuryl esters of N-phenyluracils with optionally further substituted thiolactic acid groups are described in JP09188676.
  • WO2017 / 202768 while WO2018 / 019842 describes the use of specifically substituted N-phenyluracils for combating certain dicotyledon weeds that have specific resistance to established herbicides.
  • Crop crops can be used.
  • the present invention relates to substituted N-phenyluracils of the general formula (I) or their salts
  • R 1 represents hydrogen, (Ci-C 8 ) -haloalkyl
  • R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-Cs) -alkoxy,
  • R 3 represents hydrogen, halogen, (Ci-Cs) -alkoxy
  • R 4 represents halogen, cyano, NO2, C (0) NH 2 , C (S) NH 2 , (Ci-C 8 ) -haloalkyl, (C 2 -C 8 ) -alkynyl,
  • R 5 , R 6 and R 7, independently of one another, represent hydrogen, halogen, cyano, (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-Cs) -alkoxy, (Ci-Cs) -haloalkoxy stand,
  • G is unbranched or branched (Ci-C 8 ) -alkylene
  • R 8 for hydrogen, (Ci-Cs) -alkyl, (Ci-Cs) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl,
  • R 9 represents hydrogen or (Ci-C 8 ) -alkyl
  • R 1 1 and R 12 are identical or different and are independently hydrogen, (Ci-Cs) alkyl,
  • R 1 1 and R 12 with the nitrogen atom to which they are attached, a fully saturated or
  • R 13 for hydrogen, (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, ( C 4 -Cio) -halocycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl,
  • R 14 for hydrogen, (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, ( C 4 -Cio) -halocycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl,
  • X and Y independently represent O (oxygen) or S (sulfur).
  • Preferred subject matter of the invention are compounds of the general formula (I), in which R 1 is hydrogen, (Ci-C 6 ) -haloalkyl,
  • R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-C 6 ) -alkoxy,
  • R 3 represents hydrogen, halogen, (Ci-C 6 ) -alkoxy
  • R 4 represents halogen, cyano, N0 2 , C (0) NH 2 , C (S) NH 2 , (Ci-C 6 ) -haloalkyl, (C 2 -C 6 ) -alkynyl,
  • R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (Ci-C 6 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (Ci-C 6 ) -alkoxy, (Ci-C 6 ) -Haloalkoxy stand,
  • G is unbranched or branched (Ci-C 6 ) -alkylene
  • R 8 for hydrogen, (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl,
  • R 9 represents hydrogen or (Ci-G,) - alkyl
  • R 8 and R 10 with the carbon atom to which they are attached are a fully saturated or
  • R 11 and R 12 are identical or different and independently represent hydrogen, (Ci-C 7 ) -alkyl,
  • R 11 and R 12 with the nitrogen atom to which they are attached are fully saturated or
  • R 13 for hydrogen, (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Ci 0 ) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4 -Cio) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -al
  • R 14 for hydrogen, (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4- Cio) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, aryl
  • X and Y independently represent O (oxygen) or S (sulfur).
  • Particularly preferred subject matter of the invention are compounds of the general formula (I) in which R 1 is hydrogen, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-Ce) -alkoxy,
  • R 3 represents hydrogen, halogen, (GG) -alkoxy
  • R 4 represents halogen, cyano, NO2, C (0) NH 2 , C (S) NH2, (Ci-Ce) -haloalkyl, (CA-C r ,) - Alk in ⁇ l,
  • R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (Ci-G,) - alkyl.
  • (GG) -haloalkoxy stand,
  • G stands for unbranched or branched (G-G) -alkylene
  • R 8 for hydrogen, (Ci-G,) - alkyl. (Ci-Ce) -haloalkyl, aryl, aryl- (Ci-Ce) -alkyl, heteroaryl,
  • R 9 represents hydrogen or (Ci-G) -alkyl
  • R 8 and R 10 with the carbon atom to which they are attached are a fully saturated or
  • R 1 1 and R 12 are identical or different and are each independently hydrogen, (C 'i-G,) - alkyl.
  • R 1 1 and R 12 with the nitrogen atom to which they are attached, a fully saturated or
  • R 13 for hydrogen, (Ci-C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -G,) - haloalkenyl.
  • R 14 for hydrogen, (GC 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl, (C 1 -C 10 ) -haloalkyl , (C 2 -C ( ,) - haloalkynyl.
  • X and Y independently represent O (oxygen) or S (sulfur).
  • R 1 represents hydrogen
  • R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-l-yloxy, but-1-yloxy,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-l-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-l-yloxy, 1,1 -Dimethyleth-l-yloxy stands,
  • R 4 for fluorine, chlorine, bromine, cyano, NO2, C (0) NH 2 , C (S) NH2, trifluoromethyl, difluoromethyl,
  • R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl , 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,
  • X and Y independently of one another represent O (oxygen) or S (sulfur) and
  • Q for one of the following specifically named groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q-195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 says:
  • R 1 represents hydrogen
  • R 2 represents fluorine
  • R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy
  • R 4 represents fluorine, chlorine, bromine, cyano, NO 2 , C (0) NH 2 , C (S) NH 2 , trifluoromethyl, ethynyl, propyne 1- yl stands,
  • R 5 , R 6 and R 7 independently represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, G for methylene, (methyl) methylene, (ethyl) methylene, (dimethyl) methylene, ethylene, n-propylene, (1-methyl) ethyl-1-ene, (2-methyl) ethyl-1-ene, n-butylene , 1-methylpropyl-1-en, 2-methylpropyl -
  • 2-ethylethyl-1-ene 1- (prop-1-yl) ethyl-1-ene, 2- (prop-1-yl) ethyl-1-ene, 1- (prop-2-yl) ethyl-1 -en, 2- (prop-2-yl) ethyl-l-ene, n-pentylene, 1-methylbutyl-l-ene, 2-methylbutyl-l-ene, 3-methylbutyl-l-ene, 4-methylbutyl- l-ene, 1,1-dimethylpropyl-l-ene, 2,2-dimethylpropyl-l-ene, 3,3-dimethylpropyl-l-ene, 1,2-dimethylpropyl-l-ene, 1,3-dimethylpropyl- l-ene, 1-ethylpropyl-l-ene, n-hexylene,
  • X and Y independently of one another represent O (oxygen) or S (sulfur) and
  • Q for one of the above-mentioned groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q- 195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 stands.
  • R 1 represents hydrogen
  • R 2 represents fluorine
  • R 3 stands for fluorine
  • R 4 represents chlorine, bromine, cyano, NO2, C (0) NH 2 , C (S) NH2,
  • R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl,
  • G for methylene (methyl) methylene, (ethyl) methylene, (dimethyl) methylene, ethylene, n-propylene, (1-methyl) ethyl-1-ene, (2-methyl) ethyl-1-ene, n-butylene , 1-methylpropyl-1-en, 2-methylpropyl-1-en, 3-methylpropyl-1-en, n-pentylene, n-hexylene,
  • X and Y independently represent O (oxygen) or S (sulfur) and
  • Q for one of the above-mentioned groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q- 195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 stands.
  • R 1 represents hydrogen
  • R 2 represents fluorine
  • R 3 stands for fluorine
  • R 4 stands for chlorine, bromine, cyano, NO2,
  • R 5 represents hydrogen
  • R 6 represents hydrogen, fluorine, chlorine, bromine,
  • R 7 represents hydrogen
  • G stands for methylene
  • X and Y independently of one another represent O (oxygen) or S (sulfur) and
  • Q for one of the above-mentioned groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q- 195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 stands.
  • the very particularly particularly preferred subject matter of the invention are compounds of the general formula (I) in which
  • R 1 represents hydrogen
  • R 2 represents fluorine
  • R 3 stands for fluorine
  • R 4 stands for chlorine, bromine, cyano, NO2,
  • R 5 represents hydrogen
  • R 6 represents hydrogen, fluorine
  • R 7 represents hydrogen
  • G stands for methylene
  • X stands for O (oxygen) or S (sulfur),
  • Q for one of the above-mentioned groupings Ql to Q-35, Q-41, Q-42, Q-71 to Q-80, Q-115, Q-120, Q-152 to Q-155, Q-166 to Q-170, Q-176 to Q-206, Q-211 to Q-214, Q-280 to Q-358, Q-362 to Q-370, Q-405, Q-408 to Q-410, Q- 421 to Q-429.
  • R 1 represents hydrogen
  • R 2 represents fluorine
  • R 3 stands for fluorine
  • R 4 stands for chlorine, bromine, cyano, NO2,
  • R 5 represents hydrogen
  • R 6 represents hydrogen, fluorine
  • R 7 represents hydrogen
  • G stands for methylene
  • X stands for O (oxygen) or S (sulfur),
  • Q for one of the above-mentioned groupings Ql, Q-2, Q-6, Q-23, Q-26, Q-31, Q-41, Q-71, Q-72, Ql 15, Q-154, Q -166, Q-176, Q-201, Q-211, Q-280, Q-286, Q-288, Q-301, Q-350, Q-366, Q-367, Q-368, Q-405 , Q-421, Q-422, Q-424.
  • radical definitions given above in general or in areas of preference apply both to the end products of the general formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation.
  • the compounds can form tautomers by hydrogen shift which structurally formally would not be covered by the general formula (I), then these tautomers are nevertheless included in the definition of the compounds of the general formula (I) according to the invention, if not a particular tautomer is under consideration.
  • many carbonyl compounds can exist both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).
  • the compounds of the general formula (I) can be present as stereoisomers, depending on the nature and linkage of the substituents.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained during the preparation by customary separation methods.
  • the chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale to produce test samples for biological testing.
  • stereoisomers can be selectively produced by using stereoselective reactions using optically active starting materials and / or auxiliaries.
  • the invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not indicated with their specific stereoform, and to mixtures thereof.
  • the purification can also be done by
  • Suitable isolation, purification and stereoisomer separation processes for compounds of the general formula (I) are methods which are generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatography processes, especially column chromatography and HPFC (high pressure liquid chromatography), distillation , optionally under reduced pressure, extraction and other processes, any remaining mixtures can usually be separated by chromatographic separation, for example on chiral solid phases.
  • processes such as crystallization, e.g. diastereomeric salts, which can be obtained from the diastereomeric mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable.
  • the general rule for the designation of chemical groups is that the connection to the framework or the rest of the molecule takes place via the last-mentioned structural element of the chemical group in question, ie, in the case of (C2-Cs) -alkenyloxy, via the oxygen atom, and in the case of heterocyclyl (Ci-C 8 ) -alkyl or (Ci-C 6 ) -alkoxy- (Ci-C ö ) -alkoxy- (Ci-Ce) -alkyl in each case via the C atom of Alkyl group.
  • alkylsulfonyl on its own or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms e.g. (but not limited to) (Ci-C 6 ) -alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylp
  • Heteroarylsulfonyl stands for optionally substituted pyridylsulfonyl
  • Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio on its own or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8 or 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (Ci-G,) - or (Ci-C- alkylthio, e.g. (but not limited to) (Ci- C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1- Methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a via one
  • (but not limited to) (Ci-C 6 ) -Alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2 -Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentyl
  • Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (GG) -alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1
  • Alkenyloxy denotes an alkenyl radical bonded via an oxygen atom
  • alkynyloxy denotes an alkynyl radical bonded via an oxygen atom such as (C2-C10) -, (C 2 -C 6 ) - or (C2-C4) -alkenoxy or (C3-C10) -, (C3-C6) or (C3-C4) alkinoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
  • the number of carbon atoms relates to the alkyl radical in the
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynyl carbonyl group.
  • the number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • the number of C atoms relates to the alkyl radical in the alkylcarbonyloxy group.
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes multicyclic systems such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkyl, alkylthio, haloalkyl Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris- [alkyl] silyl, bis- [alkyl] arylsilyl, bis- [alkyl] alkylsilyl, tris-
  • Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
  • heterocyclic radical contains at least one heterocyclic ring
  • heterocyclic ring in which at least one carbon atom has been replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and can be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused to other carbocyclic or heterocyclic rings.
  • heterocyclyl In the case of optionally substituted heterocyclyl, multicyclic systems are also included, such as, for example, 8-aza-bicyclo [3.2.1] octanyl, 8-aza-bicyclo [2.2.2] octanyl or 1-aza-bicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl are also included.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms should be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3- Dihydro-1H-pyrrole-
  • 3-ring and 4-ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group N,
  • O and S such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1- or 2- or
  • 1,2-dithiolan-3- or 4-yl 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1,2,4-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l, 4,2-diox
  • heterocycles listed above are preferred, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, additionally also oxo and thioxo.
  • the oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams.
  • the oxo group can also occur on the hetero-ring atoms, which can exist in different oxidation states, e.g. with N and S, and then form, for example, the divalent groups N (O), S (O) (also SO) and S (0) 2 (also briefly SO2) im heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds
  • heteroaryls are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; lH pyrrole
  • Carbon atoms are part of another aromatic ring, so it is a matter of fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatic.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g.
  • heteroaryl are also 5- or 6-membered benzofused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran 5- yl, l-Benzo Domainan-6-yl, l-Benzo liesan-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5- yl, l-benzothiophen-6-yl, l-benzothiophen,
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted and in the latter case is referred to as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • the prefix “bis” also includes the combination of different alkyl radicals, e.g. B. methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means partially or completely substituted alkyl, alkenyl or alkynyl, e.g. monohaloalkyl, by identical or different halogen atoms
  • ( Monohaloalkyl) such as e.g. B. CH 2 CH 2 CI, C 1-4 CTTBr, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as e.g.
  • Polyhaloalkyl such as e.g. B. CHFC1 CH 2, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3;
  • perhaloalkyl also includes the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, where the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as. B. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • Partially fluorinated haloalkyl means a straight or branched chain, saturated one
  • Hydrocarbon which is substituted by different halogen atoms with at least one fluorine atom, all other halogen atoms optionally present being selected from the group fluorine, chlorine or bromine, iodine.
  • halogen atoms can be
  • Partially fluorinated haloalkyl also includes the complete substitution of the straight-chain or branched chain by halogen with the participation of at least a fluorine atom.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 C1; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (Ci-C-alkyl) means an abbreviation for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to
  • Range for carbon atoms ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals with a larger specified range of carbon atoms e.g. B. "(Ci-C 6 ) -Alkyl”, accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including those in composite radicals, are preferably the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or, in the case of unsaturated groups, with 2 to 6 carbon atoms.
  • Alkyl radicals including those in the composite radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Preference is given to radicals with a double bond or
  • alkenyl also includes, in particular, straight-chain or branched open-chain ones
  • Hydrocarbon radicals with more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, e.g.
  • alkynyl also includes, in particular, straight-chain or branched open-chain ones
  • -Alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl -2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl , 4-pentynyl, 1-methyl -2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl - 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl -2-pentyn
  • cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, AMino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, with substituents with a double bond on the
  • Cycloalkyl radical e.g. B. an alkylidene group such as methybdenum are included.
  • multicyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 -yl , Bicyclo [1.1.1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2. l.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 carbon atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, with substituents with a double bond on the cycloalkenyl radical, e.g. B. an alkylidene group such as methylidene are included.
  • substituents with a double bond on the cycloalkenyl radical e.g.
  • an alkylidene group such as methylidene are included.
  • alkylidene e.g. B. also in the form (Ci-Cio) -Alkyliden, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • alkylidene e.g. B. also in the form (Ci-Cio) -Alkyliden, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • alkylene e.g. B. also in the form (Ci-Cs) -alkylene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded to other groups in two positions.
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
  • Alkoxyalkyl stands for an alkoxy radical bonded via an alkyl group and “alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl stands for an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bonded via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy radical bonded via an alkyl group.
  • Haloalkoxyalkyl stands for a bonded haloalkoxy radical and “haloalkylthioalkyl” means a haloalkylthio radical bonded via an alkyl group.
  • ..Arylalkyl stands for an aryl radical bonded via an alkyl group
  • Heteroarylalkyl means a heteroaryl radical bonded via an alkyl group
  • Heterocyclylalkyl means a heterocyclyl radical bonded via an alkyl group.
  • Cy cloalkylalkyl stands for a cycloalkyl radical bonded via an alkyl group, e.g. B. (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.
  • Arylalkenyl stands for an aryl radical bonded via an alkenyl group
  • Heteroarylalkenyl means a heteroaryl radical bonded via an alkenyl group
  • Heterocyclylalkenyl means a heterocyclyl radical bonded via an alkenyl group.
  • Arylalkynyl stands for an aryl radical bonded via an alkynyl group
  • Heteroarylalkynyl means a heteroaryl radical bonded via an alkynyl group
  • Heterocyclylalkynyl means a heterocyclyl radical bonded via an alkynyl group.
  • haloalkylthio on its own or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably with 1 to 8 or 1 to 6
  • Carbon atoms such as (Ci-Cs) -, (CrG,) - or (Ci-C- haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-l-ylthio, 2,2 , 2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • Halocycloalkyl and “Halocycloalkenyl” mean by the same or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, for example 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1 -Trifluoromethylcycloprop-1-yl, 2- trifluoromethylcycloprop-1 -yl, 1-chlorocycloprop-1 -yl, 2-chlorocycloprop-1 -yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl,
  • “trialkylsilyl” - on its own or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8 or 1 to 6
  • Carbon atoms such as tri - [(Ci-C 8 ) -, (Ci-G,) - or (Ci-C4) -alkyl] silyl for example (but not limited to) trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (iso-propyl) silyl, tri- (n-butyl) silyl, tri- (1-methylprop-l-yl) silyl, tri- (2-methylprop-l-yl) silyl, tri (l, 1-dimethyleth-1-yl) silyl, tri (2,2-dimethyleth-1 -yl) silyl.
  • “Trialkylsilylalkynyl” stands for a trialkylsilyl radical bonded via an alkynyl group.
  • the substituted N-phenyluracils of the general formula (I) according to the invention can be prepared on the basis of known processes.
  • the synthetic routes used and investigated are based on commercially available or easily prepared heteroaromatic amines and correspondingly substituted hydroxy esters.
  • the groupings G, Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X and Y of the general formula (I) have those defined above in the following schemes
  • a suitable polar aprotic solvent e.g. N, N-dimethylformamide
  • a suitable polar aprotic solvent e.g. N, N-dimethylformamide
  • pyrimidine-2,4-dione for example, but not limiting, 3- (4-chloro-2-fluorophenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione, transferred ( Scheme 1).
  • a suitable reagent e.g.
  • Tris dibenzylideneacetone dipalladium (0)
  • a suitable ligand e.g. 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene
  • a suitable base e.g. diispropyl (ethyl) amine
  • polar aprotic solvents e.g dioxane
  • R 5 , R 6 , R 7 are exemplary but not limiting for hydrogen
  • X are exemplary but not limiting for sulfur
  • Y are exemplary but not limiting for oxygen
  • G are exemplary but not limiting for CH 2 .
  • the corresponding intermediate (II) described in Scheme 2 by way of example, but not by way of limitation, can be prepared by reaction with a suitable, optionally further substituted iodoalkanoic acid ester (in Scheme 3, for example, but not by way of limitation, an iodoacetic acid ester) using a suitable base (e.g.
  • Reaction conditions [using a suitable acid such as e.g. B. hydrochloric acid or acetic acid in the case of (IVa) or trifluoroacetic acid (TFA) in the case of (IVb)] can be converted into the corresponding free acid (V).
  • a suitable acid such as e.g. B. hydrochloric acid or acetic acid in the case of (IVa) or trifluoroacetic acid (TFA) in the case of (IVb)
  • a suitable acid such as e.g. B. hydrochloric acid or acetic acid in the case of (IVa) or trifluoroacetic acid (TFA) in the case of (IVb)
  • TFA trifluoroacetic acid
  • HOBt 1-hydroxybenzotriazole
  • EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
  • HATU 0- ( 7-Azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4 , 6-trioxide
  • suitable bases e.g. diisopropylethylamine, triethylamine
  • a suitable polar aprotic solvent e.g.
  • the desired substituted N-phenyluracils of the general formula (Ia) can be prepared.
  • the ethyl ester (IVa) can be converted into the corresponding, desired substituted N-phenyluracil of the general formula (Ia) by coupling with a suitable compound QH with the mediation of a suitable Fewis acid (e.g. indium (III) chloride) (cf. WO2011 / 1307088 ).
  • Nitration reagent and subsequent N-methylation with a suitable methylation reagent gives the desired intermediate, here by way of example but not limitation 3- (2,5-difluoro-4-nitro) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2, 4-dione (via).
  • R 1 is by way of example but not limiting for hydrogen
  • R 2 is by way of example but not limiting for fluorine
  • R 3 is by way of example but not limiting for fluorine
  • R 4 is by way of example but not limiting for nitro.
  • a suitable base e.g. potassium carbonate
  • a suitable polar aprotic solvent e.g. N, N -Dimethylformamide (DMF)
  • DMF N, N -Dimethylformamide
  • the intermediate (VII) used for this can be synthesized in a multistage manner starting from commercially available 2-chloro-3-nitropyridine via (i) base-mediated coupling (e.g.
  • a suitable polar-aprotic solvent e.g. Tetrahydrofuran or dioxane
  • a suitable reducing agent e.g. hydrogen, palladium on carbon in a suitable polar protic solvent
  • diazotization with a suitable diazotization reagent, e.g. tert-butyl nitrite (t -BuONO), boron trifluoride etherate (BF -OEt) in suitable polar aprotic solvents (e.g.
  • R 3 is exemplary but not limiting for fluorine
  • R 4 is exemplary, but not limiting for chlorine or nitro
  • R 5 , R 6 , R 7 are exemplary but not limiting for hydrogen
  • X and Y are exemplary, but not limiting for oxygen
  • G are exemplary, but not limiting, of CH 2 .
  • a suitable substituted 2-carbonylalkylthio-3-hydroxypyridine VIII
  • a suitable base e.g. potassium carbonate
  • a suitable polar aprotic solvent e.g. N, N-dimethylformamide (DMF)
  • X 0 (oxygen)
  • Y S (sulfur).
  • the intermediate (VIII) used for this can be prepared by multistage synthesis analogous to the synthesis of the intermediate (VII) described in Scheme
  • nitro group in compound (Id) can then be converted into a halogen substituent (eg chlorine, bromine) by reduction and subsequent Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ie) can be obtained in this way.
  • a halogen substituent eg chlorine, bromine
  • R 1 and R 2 have the meanings according to the invention above.
  • R 3 is by way of example but not limiting for fluorine
  • R 4 is by way of example but not limiting for chlorine or nitro
  • R 5 , R 6 , R 7 are by way of example but not limiting for hydrogen
  • X is by way of example but not limiting for oxygen
  • Y stands for sulfur by way of example but not by way of limitation
  • G is by way of example but not by way of limitation for CH2.
  • the intermediate, further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-diones (II) can also be converted into the desired compounds of the general formula (If) according to the invention, in which X and Y are sulfur (S), are converted (Scheme 7) after the compounds (III) in a first step with the aid of a suitable optionally further substituted iodo-thiopyridine with the use of a suitable base or with the use of a suitable one
  • Transition metal catalyst e.g. tris (dibenzylideneacetone) dipalladium (0)
  • a suitable ligand e.g. 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene
  • a suitable base e.g. diispropyl ( ethyl amine) in a suitable polar-aprotic solvent (e.g. dioxane)
  • No. 1.1-1 2-Methoxyethyl - ⁇ [3 - ( ⁇ 2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H ) -yl] phenyl ⁇ sulfanyl) pyridin-2-yl] oxy ⁇ acetate.
  • reaction mixture was stirred at room temperature for 1 h, then cooled to a temperature of -30 ° C., and 2-fluoro-4-chlorophenyl isocyanate (12.0 g, 70.0 mmol) was added. After the addition was complete, the resulting reaction mixture was stirred for 4 hours at room temperature and then poured into ice water. After the addition of ethyl acetate and acidification with 1N hydrochloric acid, the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered off and concentrated under reduced pressure.
  • reaction mixture was then stirred for 2 hours at a temperature of 50 ° C. and, after cooling to room temperature, combined with water (5 mL) and dichloromethane and extracted. The combined organic phases were dried over sodium sulfate, filtered off and under
  • the batch was stirred for 2 h at RT, left to stand for 4 d at RT, and a further 0.25 equivalents each of 1-hydroxy-1H-benzotriazole hydrate, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 3-methoxy-1-propanol were added admitted.
  • the mixture was stirred at RT for 6 h, left to stand at RT overnight and the solvent was removed.
  • Dichloromethane became [(3- ⁇ 2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H) -yl] phenoxy ⁇ pyridine) -2-yl) oxy] acetic acid (120 mg, 0.25 mmol) was added and then 1-hydroxy-1H-benzotriazole hydrate (49 mg, 0.32 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (61 mg, 0.32 mmol) and 4-dimethylaminopyridine (10 mol%) are added.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.1-1 to 1.1-440 of table 1.1 are thus due to the meaning of the respective entries No. 1 to 440 for Q der
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections 1.2-1 to 1.2-440 of Table 1.2 are thus identified by the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections 1.3-1 to 1.3-440 of Table 1.3 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (F4) are the compounds F4-1 to F4-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.4-1 to F4-440 of table F4 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.5-1 to 1.5-440 of Table 1.5 are thus due to the meaning of the respective entries No. 1 to 440 for Q der
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections 1.6-1 to 1.6-440 of Table 1.6 are thus identified by the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections 1.7-1 to 1.7-440 of Table 1.7 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections 1.8-1 to 1.8-440 of Table 1.8 are thus identified by the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table F9 Preferred compounds of the formula (F9) are the compounds F9-1 to F9-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F9-1 to F9-440 of table F9 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table 1.10 Preferred compounds of the formula (F 10) are the compounds F 10-1 to F 10-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F 10-1 to F 10-440 of Table F 10 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table E li Preferred compounds of the formula (1.11) are the compounds 1.11-1 to F l-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections F 11-1 to F 11-440 of Table F 11 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.12: Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.12-1 to 1.12-440 of Table 1.12 are thus due to the meaning of the respective entries No. 1 to
  • Table 1.13 Preferred compounds of the formula (F13) are the compounds F 13-1 to F 13-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F 13-1 to F 13-440 of table F13 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table E14 Preferred compounds of the formula (E14) are the compounds E 14-1 to E 14-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E 14-1 to E 14-440 of table E14 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table E 15 Preferred compounds of the formula (E 15) are the compounds E 15-1 to E 15-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E 15-1 to E 15-440 of Table E 15 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.16-1 to 1.16-440 of table 1.16 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.17 Preferred compounds of the formula (F 17) are the compounds F 17-1 to F 17-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F 17-1 to F 17-440 of table F 17 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table E l 8 Preferred compounds of the formula (E l 8) are the compounds E l 8-1 to E l 8-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E 18-1 to E 18-440 of Table E 18 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.19: Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.19-1 to 1.19-440 of Table 1.19 are thus due to the meaning of the respective entries No. 1 to
  • Table E20 Preferred compounds of the formula (E20) are the compounds E20-1 to E20-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E20-1 to E20-440 of table E20 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.21 Preferred compounds of the formula (F21) are the compounds F21-1 to F21-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F21-1 to F21-440 of table F21 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table E22 Preferred compounds of the formula (E22) are the compounds E22-1 to E22-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E22-1 to E22-440 of table E22 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.23-1 to 1.23-440 of table 1.23 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table E24 Preferred compounds of the formula (E24) are the compounds E24-1 to E24-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E24-1 to E24-440 of table E24 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.25 Preferred compounds of the formula (F25) are the compounds F25-1 to F25-440, in which Q has the meanings given in Table 1 in the respective line. The connections F25-1 to F25-440 in table F25 are therefore clear due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.26-1 to 1.26-440 of Table 1.26 are thus due to the meaning of the respective entries No. 1 to
  • Table 1.27 Preferred compounds of the formula (F27) are the compounds F27-1 to F27-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F27-1 to F27-440 of table F27 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table E28 Preferred compounds of the formula (E28) are the compounds E28-1 to E28-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E28-1 to E28-440 of table E28 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.29 Preferred compounds of the formula (F29) are the compounds F29-1 to F29-440, in which Q has the meanings of Table 1 given in the respective line.
  • the connections F29-1 to F29-440 of table F29 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.30-1 to 1.30-440 of Table 1.30 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table E31 Preferred compounds of the formula (E31) are the compounds E31-1 to E31-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E31-1 to E31-440 of table E31 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table E32 Preferred compounds of the formula (E32) are the compounds E32-1 to E32-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E32-1 to E32-440 of table E32 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • Table 1.33: Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.33-1 to 1.33-440 of Table 1.33 are thus due to the meaning of the respective entries No. 1 to
  • Table 1.34 Preferred compounds of the formula (F34) are the compounds F34-1 to F34-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections F34-1 to F34-440 in table F34 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
  • Table E35 Preferred compounds of the formula (E35) are the compounds E35-1 to E35-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections E35-1 to E35-440 of table E35 are thus due to the meaning of the respective entries No. 1 to
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-440, in which Q has the meanings given in Table 1 in the respective line.
  • the connections 1.36-1 to 1.36-440 of Table 1.36 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
  • NMR data of selected examples The 'H-NMR data of selected examples of compounds of the general formula (I) are given in two different ways, namely (a) classical NMR evaluation and interpretation or (b) in the form of 1H- NMR peak lists according to the method described below. a) classical NMR interpretation
  • the 'H-NMR data of selected examples can also be noted in the form of' H-NMR peak lists. For each signal peak, first the d-value in ppm and then the signal intensity is listed in round brackets. The d-value - signal intensity number pairs of different signal peaks are listed separated from each other by semicolons.
  • the peak list of an example therefore has the form: di (intensity ?: d 2 (intensity2);; d ⁇ (intensity ;; d h (intensityn)
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the real relationships between the signal intensities. Broad signals can have multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum.
  • To calibrate the chemical shift of 1H-NMR spectra we use tetramethylsilane and / or the chemical shift of the
  • Solvent especially in the case of spectra measured in DMSO.
  • the tetramethylsilane peak can therefore appear in NMR peak lists, but does not have to be.
  • the lists of 'H-NMR peaks are similar to the classic' H-NMR printouts and thus usually contain all peaks that are listed in a classic NMR interpretation.
  • they can show solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
  • connection signals in the delta range of solvents and / or water our lists of 'H-NMR peaks show the usual solvent peaks, for example peaks from DMSO in DMSO-D 6 and the peak from water, which are usually have a high intensity on average.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example, with a purity of> 90%).
  • Such stereoisomers and / or impurities can be typical of the particular manufacturing process. Your peaks can thus help to identify the reproduction of our manufacturing process using “by-product fingerprints”.
  • the present invention also relates to the use of one or more
  • inventive compounds of the general formula (I) and / or their salts as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts , each as defined above,
  • herbicide and / or plant growth regulator preferably in crops of useful and / or ornamental plants.
  • the present invention also relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) according to the invention and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, to the (harmful) Plants, (harmful) plant seeds, the soil in which or on which the (harmful) plants grow or the area under cultivation is applied.
  • the present invention also relates to a method for controlling undesirable plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferred or particularly preferred
  • the present invention also relates to methods of combating
  • Reproductive organs such as tubers or sprouts with buds
  • the soil in which or on which the plants grow e.g. the soil of cultivated land or non-cultivated land
  • the cultivated area i.e. the area on which the plants will grow
  • the compounds according to the invention or the agents according to the invention can be applied, for example, by pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or post-emergence methods.
  • Weed flora called, through which the compounds according to the invention can be controlled, without the mentioning of them being intended to restrict to certain species.
  • one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamentals, the useful plants or ornamentals in a preferred embodiment are transgenic plants.
  • the compounds of general formula (I) according to the invention and / or their salts are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
  • Monocotyledonous harmful plants of the genera Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragloaim, Festylochata , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • the compounds according to the invention are applied to the surface of the earth (pre-emergence method) before the harmful plants (weeds and / or weeds) germinate, either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage, but then continue to grow and finally die off completely after three to four weeks.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledon and dicotyledon weeds, crops of economically important crops, for example dicotyledon crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
  • the compounds according to the invention (depending on their particular structure and the amount applied) have excellent growth-regulatory properties in crop plants. They intervene in a regulating manner in the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesired vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledon and dicotyledon crops, since it can reduce or completely prevent storage, for example.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered plants or plants that have been modified by conventional mutagenesis.
  • the transgenic plants are generally distinguished by particularly advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate, for example, to the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered starch quality or those with different
  • Fatty acid composition of the harvested material known.
  • transgenic crops preference is given to using the compounds according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereals such as wheat, barley, rye, oats, millet, rice and maize or else crops of sugar beet, cotton, Soy, rapeseed, potato, tomato, pea and other vegetables.
  • cereals such as wheat, barley, rye, oats, millet, rice and maize or else crops of sugar beet, cotton, Soy, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds according to the invention can preferably also be used as herbicides in
  • Crops of useful plants are used which are resistant to the phytotoxic effects of herbicides or which have been made resistant by genetic engineering.
  • the active compounds can also be used for combating harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by particularly advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate, for example, to the crop in terms of quantity, Quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered starch quality or those with different
  • Fatty acid composition of the harvested material known. Further special properties can be found in a tolerance or resistance to abiotic stressors e.g. heat, cold, drought, salt and ultraviolet radiation.
  • the compounds of the general formula (I) can preferably be used as herbicides in
  • Crops of useful plants are used which are resistant to the phytotoxic effects of herbicides or which have been made resistant by genetic engineering.
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences.
  • base exchanges can be carried out, partial sequences can be removed or natural or synthetic sequences can be added.
  • RNA for example, achieved by expressing at least one corresponding antisense RNA, one sense RNA to achieve a cosuppression effect or expressing at least one appropriately constructed ribozyme that specifically cleaves transcripts of the abovementioned gene product.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough, to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein can be localized in any desired compartment of the plant cell.
  • the coding region can be linked with DNA sequences which ensure the localization in a certain compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can be any plant
  • the compounds (I) according to the invention can preferably be used in transgenic crops which are essential against growth substances such as dicamba or against herbicides
  • Plant enzymes e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD) inhibit or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydoxyphenylpyruvate dioxygenases
  • the active ingredients according to the invention are used in transgenic crops, in addition to the effects on harmful plants observed in other crops, effects that are specific to the application in the respective transgenic crop, for example a modified or specially expanded weed spectrum that can be controlled, often occur Application rates which can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crops.
  • cereals preferably maize, wheat, barley, rye, oats, millet or rice, pre- or post-emergence.
  • Regulation of the growth of plants also includes the case in which the active ingredient of the general formula (I) or its salt is formed from a precursor substance (“prodrug”) only after it has been applied to the plant, in the plant or in the soil.
  • the invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts are applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in which or on which the plants grow, or the area under cultivation.
  • the invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
  • component (i) of an agent according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • a herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) which are customary in crop protection and selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents which are miscible with water in any ratio at 25 ° C and 1013 mbar.
  • the compounds (I) according to the invention can be emulsifiable in the form of wettable powders
  • the invention therefore also relates to herbicidal and
  • Plant growth regulating agents which contain compounds of the general formula (I) and / or their salts.
  • the compounds of the general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemico-physical parameters are given. Possible formulation options include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions ,
  • SC Suspension concentrates
  • oil- or water-based dispersions oil-miscible solutions
  • CS Capsule suspensions
  • DP dusts
  • dressings granulates for the litter
  • granules in the form of micro, spray, lift and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • Wettable powders are preparations that are uniformly dispersible in water which, in addition to the active ingredient, besides a diluent or inert substance, also ionic and / or nonionic surfactants (wetting agents, dispersants), e.g.
  • the herbicidally active ingredients are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of an ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of an ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or
  • Polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if necessary, the addition of surfactants, such as those already listed above for the other types of formulation.
  • Emulsions e.g. oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material.
  • adhesives e.g. polyvinyl alcohol, sodium polyacrylate or mineral oils
  • Active ingredients are granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
  • Water-dispersible granules are generally produced by the customary processes such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferred 2 to 80% by weight, of active ingredients of the general formula (I) and their salts.
  • the active ingredient concentration is e.g. about 10 to 90% by weight, the remainder to 100% by weight consists of conventional formulation components. In the case of emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dusty
  • Formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned contain, if appropriate, the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and the Viscosity influencing agents.
  • formulation auxiliaries are described, inter alia, in “Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of the general formula (I) or their salts can be used as such or in the form of their preparations (formulations) with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
  • Growth regulators can be used in combination, e.g. as a finished formulation or as
  • Tank mixes The combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active ingredients to be combined.
  • Combination partners for the compounds of the general formula (I) according to the invention in mixture formulations or in the tank mix are, for example, known active ingredients which act on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate- Synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as they are for example in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited there.
  • Cultivated plants occur.
  • combinations of compounds (I) according to the invention which contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest.
  • the safeners which are used in an antidoteic content, reduce the phytotoxic side effects of the herbicides / pesticides used, for example in economically important crops such as grain (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rape, cotton and soy, preferably grain.
  • the weight ratio of herbicide (mixture) to safener generally depends on the
  • the safeners can be formulated analogously to the compounds (I) or mixtures thereof with further herbicides / pesticides and are provided and used as a finished formulation or tank mix with the herbicides.
  • the herbicide or herbicide-safener formulations in commercially available form are optionally diluted in the customary manner, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in dust form, soil granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the application rate can vary within wide limits.
  • the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence use.
  • Plant growth regulator for example as a stalk shortener in crop plants, as they have been mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to the application in
  • the application as a stalk shortener can take place in different stages of the growth of the plants. For example, use after tillering at the beginning of the
  • the treatment of the seed which includes the different seed dressing and coating techniques, is also possible.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • mixed formulations or in a tank mix are, for example, known active ingredients which act on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or
  • herbicidal mixing partners are:
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenolofen-butyl, flurenol, flurenolofen-butyl, -dimethylammonium and -fluoroglycethylammonium flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinuf-ammonium, glufosinate-
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • met.zthiazuron methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron-ester, monosulfuron, ie, N- [3-chloron, monosulfuron -4- (1-methylethyl) -phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargy
  • plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
  • Brassinolide Catechin, chlormequat Chloride, cloprop, cyclanilide, 3- (Cycloprop-l-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probemonic acid azole, jasmonic acid , maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2- (l-naphthyl)
  • Sl d compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
  • Fenchlorazole ethyl ester
  • Sl-7 ethyl carboxylate
  • Sl e compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S 1- 10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-11) ("isoxadifen-ethyl”)
  • S2 a compounds of the 8-quinolineoxyacetic acid type (S2 a ), preferably
  • S2 b compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ), preferably
  • oils effective safeners are used, such as. B.
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-Allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide
  • TI-35 (1-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
  • R A 1 (Ci-C ö ) -alkyl, (C3-C6) -cycloalkyl, where the last two radicals mentioned by VA
  • R A 2 halogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkoxy, CF 3; m A 1 or 2;
  • VA is 0, 1, 2 or 3;
  • S4 b compounds of the 4- (benzoylsulfamoyl) benzamide type of the formula (S4 b ) and their salts, as described in WO-A-99/16744,
  • R B 1 , R B 2 independently of one another are hydrogen, (Ci-Ce) -alkyl, (C3-C6) -cycloalkyl, (CVG,) -alkenyl, (-G,) -alkynyl.
  • R B 3 halogen, (Ci-G) -alkyl, (Ci-C4) -haloalkyl or (Ci-G) -alkoxy and m B 1 or 2, for example those in which
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-2)
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-4) and
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe (S4-5);
  • Rc 1 , Rc 2 independently of one another are hydrogen, (GG) -alkyl, (GG) -cycloalkyl, (G-
  • Rc 3 halogen, (Ci-G -alkyl, (Ci-C- alkoxy, CF 3 and mc is 1 or 2; for example l- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • Carboxylic acid derivatives (S5) e.g.
  • Ethyl 3,4,5-triacetoxybenzoate 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A 2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • RD 1 is halogen, (Ci-C-alkyl, (Ci-C- haloalkyl, (Ci-C4) -alkoxy, (Ci-C4) -haloalkoxy,
  • R D 2 is hydrogen or (Ci-C4) -alkyl
  • RD 3 is hydrogen, (Ci-Cs) -alkyl, (C2-C4) -alkenyl, (C2-C4) -alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts, n D is an integer from 0 to 2.
  • n E is an integer from 0 to 4,
  • R E 2 (Ci-Ci ö ) -alkyl, (CVCrd-alkenyl. (C3-C6) -cycloalkyl, aryl; benzyl, halobenzyl,
  • R E 3 is hydrogen or (C iG,) - alkyl.
  • Oxabetrinil ((Z) -l, 3-Dioxolan-2-ylmethoxyimino (phenyl) acetonitril) (S 11-1), which is known as a seed dressing safener for millet against damage from metolachlor,
  • Active ingredients from the class of isothiochromanones such as methyl - [(3-oxo-lH-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS reg. No. 205121-04-6 ) (S12-1) and related compounds from WO-A-1998/13361.
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
  • Cyanamide which is known as a safener for corn against damage from imidazolinones
  • MG 191 (CAS Reg.Nr. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize, "MG 838” (CAS Reg. No. 133993-74-5)
  • Active ingredients which, in addition to a herbicidal effect against harmful plants, also have a safener effect on crop plants such as rice, such as. B.
  • CSB (1-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.
  • R H 1 denotes a (CC 6 ) -haloalkyl radical
  • R H 2 is hydrogen or halogen
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Cie) -alkyl, (C2-Cie) -alkenyl or (C2-C16) -
  • Alkynyl where each of the last-mentioned 3 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, ( Ci-C 4) alkylamino, di [(Ci-C4) -alkyl] amino, [(Ci-C 4) alkoxy] - carbonyl, [(Ci-C4) -haloalkoxy] carbonyl, (GG) Cycloalkyl.
  • das an one side of the ring is condensed with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 ) -cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring , where each of the last-mentioned 4 radicals is unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) -alkoxy, (GG) -Haloalkoxy.
  • (GG) -Alkylamino Di [(Ci- C 4 ) alkyl] -amino, [(Ci-C 4 ) alkoxy] -carbonyl, [(Ci-C 4 ) Haloalkoxy] carbonyl, (GC ⁇ ) - cycloalkyl that is unsubstituted or substituted, phenyl that is unsubstituted or substituted, and heterocyclyl that is unsubstituted or is substituted, is substituted, means or
  • RH 3 is (Ci-C 4 ) -alkoxy, (C2-C 4 ) -alkenyloxy, (C2-G,) -alkinyloxy or (C2-C 4 ) -haloalkoxy and
  • R H 4 is hydrogen or (Ci-C 4 ) -alkyl or
  • RH 3 and RH 4 together with the directly bonded nitrogen atom form a four- to eight-membered
  • heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, (Ci- C 4 ) -alkyl, (Ci-G-haloalkyl, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy and (Ci-C 4 ) -alkylthio is substituted.
  • Preferred safeners in combination with the compounds of the general formula (I) according to the invention and / or their salts, in particular with the compounds of the formulas (E 1) to (1.34) and / or their salts are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl ester , Isoxadifen-ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 and S4-5, and particularly preferred safeners are: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl and Mefenpyr-Diethyl.
  • Wooden fiber pots are laid out in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated in the single-leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of 600 l / ha.
  • Tables A1 to A15 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 on various harmful plants and an application rate corresponding to 20 g / ha and lower, which were obtained according to the aforementioned test procedure.
  • Table Al
  • Tables A16 to A19 below show the crop compatibility of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 at an application rate corresponding to 5 or 20 g / ha, which were observed in tests according to the above-mentioned test procedure. The effects observed on selected crop plants are given in comparison with the untreated controls (values in%).
  • compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants, such as, for example, on post-emergence treatment.
  • Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants were placed in plastic or organic plant pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of the equivalent of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • Tables B1 to B 13 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 on various harmful plants and one Application rate corresponding to 80 g / ha or lower, which was obtained according to the test procedure mentioned above, is shown.
  • Table B 13 Tables B14 to B16 below show the crop compatibility of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 at an application rate corresponding to 20 g / ha, which were observed in tests according to the above test procedure. The effects observed on selected crop plants are given in comparison with the untreated controls (values in%).
  • Harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Veronica tricolorica or an active substance of 0.0 kg less per hectare, as well as a good tolerance to crop plants in organisms such as Zea mays, Glycine max and Triticum aestivum at an application rate of 0.02 kg per hectare.

Abstract

The invention relates to substituted N-phenyl uracils of the general formula (I) or salts (I) thereof, wherein the groups in the general formula (I) are as defined in the description, and to the use thereof as herbicides, more specifically for controlling weeds and/or weed grasses in crops of cultivated plants and/or as plant-growth regulators for influencing the growth of crops of cultivated plants.

Description

Bayer AG Bayer AG
Substituierte N-Phenyluracile sowie deren Salze und ihre Verwendung als herbizide Wirkstoffe Beschreibung Substituted N-phenyluracils and their salts and their use as herbicidal active ingredients Description
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsem in Nutzpflanzenkulturen. The invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and grass weeds in crops of useful plants.
Speziell betrifft diese Erfindung substituierte N-Phenyluracile sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide, inbesondere zur Bekämpfung von Unkräutern und/oder Ungräsem in Nutzpflanzenkulturen und/oder als Pflanzenwachstumsregulatoren zur Beeinflussung des Wachstums von Nutzpflanzenkulturen. This invention specifically relates to substituted N-phenyluracils and their salts, processes for their preparation and their use as herbicides, in particular for controlling weeds and / or grass weeds in crops of useful plants and / or as plant growth regulators for influencing the growth of crops of useful plants.
Bisher bekannte Pflanzenschutzmittel zur selektiven Bekämpfung von Schadpflanzen in So far known pesticides for the selective control of harmful plants in
Nutzpflanzenkulturen oder Wirkstoffe zur Bekämpfung von unerwünschtem Pflanzenwuchs weisen bei ihrer Anwendung teilweise Nachteile auf, sei es, dass sie (a) keine oder aber eine unzureichende herbizide Wirkung gegen bestimmte Schadpflanzen, (b) ein zu geringes Spektrum der Schadpflanzen, das mit einem Wirkstoff bekämpft werden kann, (c) zu geringe Selektivität in Nutzpflanzenkulturen und/oder (d) ein toxikologisch ungünstiges Profil besitzen. Weiterhin führen manche Wirkstoffe, die als Pflanzenwachstumsregulatoren bei einigen Nutzpflanzen eingesetzt werden können, bei anderen Nutzpflanzen zu unerwünscht verminderten Emteerträgen oder sind mit der Kulturpflanze nicht oder nur in einem engen Aufwandmengenbereich verträglich. Einige der bekannten Wirkstoffe lassen sich wegen schwer zugänglicher Vorprodukte und Reagenzien im industriellen Maßstab nicht wirtschaftlich hersteilen oder besitzen nur unzureichende chemische Stabilitäten. Bei anderen Wirkstoffen hängt die Wirkung zu stark von Umweltbedingungen, wie Wetter- und Bodenverhältnissen ab. Crops of useful plants or active ingredients for controlling unwanted vegetation sometimes have disadvantages when they are used, be it that they (a) have no or inadequate herbicidal activity against certain harmful plants, (b) an insufficient spectrum of harmful plants that can be controlled with an active ingredient can be, (c) too low selectivity in crops of useful plants and / or (d) have a toxicologically unfavorable profile. Furthermore, some active ingredients which can be used as plant growth regulators in some useful plants lead to undesirably reduced yields in other useful plants or are incompatible with the cultivated plant, or only compatible with a narrow application rate range. Some of the known active ingredients cannot be produced economically on an industrial scale because of the difficult accessibility of precursors and reagents, or they have insufficient chemical stabilities. With other active ingredients, the effect depends too much on environmental conditions, such as weather and soil conditions.
Die herbizide Wirkung dieser bekannten Verbindungen, insbesondere bei niedrigen Aufwandmengen, bzw. deren Verträglichkeit gegenüber Kulturpflanzen bleiben verbesserungswürdig. The herbicidal action of these known compounds, in particular when low amounts are used, or their compatibility with crop plants, remain in need of improvement.
Es ist aus verschiedenen Schriften bekannt, daß bestimmte substituierte N-verknüpfte Aryluracile als herbizide Wirkstoffe verwendet werden können (vgl. EP408382, EP473551, EP648749, US4943309, US5084084, US5127935, W091/00278, W095/29168, WO95/30661, W096/35679, WO97/01541, WO98/25909, WO2001/39597). Die bekannten Aryluracile weisen jedoch eine Reihe von It is known from various publications that certain substituted N-linked aryluracils can be used as herbicidal active ingredients (cf. EP408382, EP473551, EP648749, US4943309, US5084084, US5127935, WO91 / 00278, WO95 / 29168, WO95 / 30661, WO96 / 35679 , WO97 / 01541, WO98 / 25909, WO2001 / 39597). The known aryluracils, however, have a number of
Wirkungslücken, insbesondere gegenüber monokotylen Unkräutern auf. Eine Reihe von herbiziden Wirkstoffkombinationen auf Basis von N-verknüpften Aryluracilen sind ebenfalls bekannt geworden (vgl. DE4437197, EP714602, WO96/07323, WO96/08151, JP11189506). Die Eigenschaften dieser Wirkstoffkombinationen waren jedoch auch nicht in allen Belangen zufriedenstellend. Effect gaps, especially against monocotyledon weeds. A number of herbicidal active ingredient combinations based on N-linked aryluracils have also become known (cf. DE4437197, EP714602, WO96 / 07323, WO96 / 08151, JP11189506). However, the properties of these active ingredient combinations were also not satisfactory in all respects.
Es ist weiterhin bekannt, daß bestimmte N-Phenyluracile mit gegebenenfalls weiter substituierten Milchsäuregruppen auch als herbizide Wirkstoffe eingesetzt werden können (vgl. JP2000/302764, JP2001/172265, US6403534, EP408382). Es ist darüber hinaus bekannt, daß N-Phenyluracile mit speziellen gegebenenfalls weiter substituierten Thiomilchsäuregruppen ebenfalls herbizide Wirkungen zeigen (vgl. W02010/038953, KR2011110420). Besondere substituierte Tetrahydrofurylester von N- Phenyluracilen mit gegebenenfalls weiter substituierten Thiomilchsäuregruppen sind in JP09188676 beschrieben. It is also known that certain N-phenyluracils with optionally further substituted lactic acid groups can also be used as herbicidal active ingredients (cf. JP2000 / 302764, JP2001 / 172265, US6403534, EP408382). It is also known that N-phenyluracils with special, optionally further substituted thiolactic acid groups also show herbicidal effects (cf. WO2010 / 038953, KR2011110420). Special substituted tetrahydrofuryl esters of N-phenyluracils with optionally further substituted thiolactic acid groups are described in JP09188676.
Ebenfalls bekannt sind substituierte Uracile, die eine N-verknüpfte und weiter substituierte Also known are substituted uracils which have an N-linked and further substituted one
Diarylethergruppe oder einen entsprechenden Heteroarylaryletherrest enthalten (vgl. US6333296, US6121201, W02001/85907, EP1122244, EP1397958, EP1422227, WO 2002/098227). Weiterhin sind hochsubstituierte N-Phenyluracile mit spezifisch substituierter Carbonylalkyloxygruppe beschrieben (vgl. WO2011/137088). Hochsubstituierte N-Pyridyluracile sind ebenfalls beschrieben (vgl. Contain diaryl ether group or a corresponding heteroaryl aryl ether radical (cf. US6333296, US6121201, WO2001 / 85907, EP1122244, EP1397958, EP1422227, WO 2002/098227). Highly substituted N-phenyluracils with specifically substituted carbonylalkyloxy groups are also described (cf. WO2011 / 137088). Highly substituted N-pyridyluracils are also described (cf.
WO2017/202768), während in WO2018/019842 die Verwendung von spezifisch substituierten N- Phenyluracilen zur Bekämpfung bestimmter dikotyler Unkräuter, die spezifische Resistenzen gegen etablierte Herbizide aufweisen, beschrieben wird. Substituierte 3-Phenyl-5-alkyl-6- (trifhiormethyl)pyrimidin-2,4(lH,3H)-dione (vgl. W02019/101551) und verwandte substituierte 3- (Pyridin-2-yl)-5-alkyl-6-(trifluormethyl)pyrimidin-2,4(lH,3H)-dione (vgl. W02019/101513) sind ebenfalls bekannt. WO2017 / 202768), while WO2018 / 019842 describes the use of specifically substituted N-phenyluracils for combating certain dicotyledon weeds that have specific resistance to established herbicides. Substituted 3-phenyl-5-alkyl-6- (trifhiormethyl) pyrimidine-2,4 (1H, 3H) -diones (cf. WO2019 / 101551) and related substituted 3- (pyridin-2-yl) -5-alkyl- 6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -diones (cf. WO2019 / 101513) are also known.
Überraschenderweise wurde nun gefunden, dass bestimmte substituierte N-Phenyluracile mit substituierter Alkylesterseitenkette oder deren Salze als Herbizide gut geeignet sind und besonders vorteilhaft als Wirkstoffe zur Bekämpfung von monokotylen und dikotylen Unkräutern in Surprisingly, it has now been found that certain substituted N-phenyluracils with substituted alkyl ester side chains or their salts are well suited as herbicides and are particularly advantageous as active ingredients for combating monocotyledon and dicotyledon weeds in
Nutzpflanzenkulturen eingesetzt werden können. Crop crops can be used.
Ein Gegenstand der vorliegenden Erfindung sind damit substituierte N-Phenyluracile der allgemeinen Formel (I) oder deren Salze The present invention relates to substituted N-phenyluracils of the general formula (I) or their salts
Figure imgf000003_0001
wonn
Figure imgf000003_0001
wonn
R1 für Wasserstoff, (Ci-C8)-Haloalkyl steht, R 1 represents hydrogen, (Ci-C 8 ) -haloalkyl,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, (Ci-Cs)-Alkoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-Cs) -alkoxy,
R3 für Wasserstoff, Halogen, (Ci-Cs)-Alkoxy steht, R 3 represents hydrogen, halogen, (Ci-Cs) -alkoxy,
R4 für Halogen, Cyano, NO2, C(0)NH2, C(S)NH2, (Ci-C8)-Haloalkyl, (C2-C8)-Alkinyl steht, R 4 represents halogen, cyano, NO2, C (0) NH 2 , C (S) NH 2 , (Ci-C 8 ) -haloalkyl, (C 2 -C 8 ) -alkynyl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (Ci-C8)-Alkyl, (Ci-C8)- Haloalkyl, (Ci-Cs)-Alkoxy, (Ci-Cs)-Haloalkoxy stehen, R 5 , R 6 and R 7, independently of one another, represent hydrogen, halogen, cyano, (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-Cs) -alkoxy, (Ci-Cs) -haloalkoxy stand,
G für unverzweigtes oder verzweigtes (Ci-C8)-Alkylen steht, G is unbranched or branched (Ci-C 8 ) -alkylene,
Q für einen Rest der Formel
Figure imgf000004_0001
steht, Q for a remainder of the formula
Figure imgf000004_0001
stands,
R8 für Wasserstoff, (Ci-Cs)-Alkyl, (Ci-Cs)-Haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, R 8 for hydrogen, (Ci-Cs) -alkyl, (Ci-Cs) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl,
(C2-C8)-Alkinyl, (C2-C8)-Alkenyl, C(0)R13, C(0)OR13, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl steht, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -alkenyl, C (0) R 13 , C (0) OR 13 , (Ci-C 8 ) -alkoxy- (Ci-C 8 ) - alkyl stands,
R9 für Wasserstoff oder (Ci-C8)-Alkyl steht, R 9 represents hydrogen or (Ci-C 8 ) -alkyl,
R10 für Cyano, N02, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, RnR12N-(Ci-C8)-alkyl, R130-(Ci-C8)-alkyl, Cyano-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyloxy- (Ci-C8)-alkyl, (C3-C8)-Cycloalkylcarbonyloxy-(Ci-C8)-alkyl, Arylcarbonyloxy-(Ci-C8)-alkyl, Heteroarylcarbonyloxy-(Ci-C8)-alkyl, Heterocyclylcarbonyloxy-(Ci-C8)-alkyl, OR13, NRnR12, SR14, S(0)R14, S02R14, R14S-(Ci-C8)-alkyl, R14(0)S-(Ci-C8)-alkyl, R1402S-(Ci-C8)-alkyl, Tris- [(Ci-C8)-Alkyl]silyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl](aryl)silyl(Ci-C8)-alkyl, [(Ci-C8)-Alkyl]- bis-(aryl)silyl-(Ci-C8)-alkyl, Tris-[(Ci-C8)-Alkyl]silyl, Bis-hydroxyboryl-(Ci-C8)-alkyl, Bis- [(Ci-C8)-alkoxy]boryl-(Ci-C8)-alkyl, Tetramethyl- 1, 3, 2-Dioxaborolan-2-yl, Tetramethyl- 1,3,2- Dioxaborolan-2-yl-(Ci-C8)-alkyl, Nitro-(Ci-C8)-alkyl, C(0)R14, Bis-(Ci-C8)-alkoxymethyl, Bis- (Ci-C8)-alkoxymethyl-(Ci-C8)-alkyl steht, oder R8 und R10 mit dem Kohlenstoffatom, an das sie gebunden sind, ein vollständig gesättigtes oder teilgesättigtes, und gegebenenfalls weiter substituiertes 3 bis 10-gliedriges monocyclisches oder bicyclisches Heterocyclyl bilden, R 10 for cyano, N0 2 , heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl, heterocyclyl- (Ci-C 8 ) -alkyl, R n R 12 N- (Ci-C 8 ) -alkyl, R 13 0- (Ci-C 8 ) -alkyl, cyano- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -Alkylcarbonyloxy- (Ci-C 8 ) -alkyl, (C3-C 8 ) -Cycloalkylcarbonyloxy- (Ci-C 8 ) -alkyl, arylcarbonyloxy- (Ci-C 8 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 8 ) -alkyl, heterocyclylcarbonyloxy- (Ci-C 8 ) -alkyl, OR 13 , NR n R 12 , SR 14 , S (0) R 14 , S0 2 R 14 , R 14 S- (Ci-C 8 ) -alkyl, R 14 (0) S- (Ci-C 8 ) -alkyl, R 14 0 2 S- (Ci-C 8 ) -alkyl, tris- [(Ci-C 8 ) -alkyl] silyl- (Ci-C 8 ) -alkyl, bis- [(Ci-C 8 ) -alkyl] (aryl) silyl (Ci -C 8 ) -alkyl, [(Ci-C 8 ) -alkyl] - bis- (aryl) silyl- (Ci-C 8 ) -alkyl, tris - [(Ci-C 8 ) -alkyl] silyl, bis- hydroxyboryl- (Ci-C 8 ) -alkyl, bis- [(Ci-C 8 ) -alkoxy] boryl- (Ci-C 8 ) -alkyl, tetramethyl- 1, 3, 2-dioxaborolan-2-yl, tetramethyl- 1,3,2-Dioxaborolan-2-yl- (Ci-C 8 ) -alkyl, nitro- (Ci-C 8 ) -alkyl, C (0) R 14 , bis- (Ci-C 8 ) -alkoxymethyl, Bis- (Ci-C 8 ) -alkoxymethyl- (Ci-C 8 ) -alkyl, or R 8 and R 10 with the carbon atom to which they are attached form a fully saturated or partially saturated, and optionally further substituted 3 to 10-membered monocyclic or bicyclic heterocyclyl,
R1 1 und R12 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-Cs)-Alkyl,R 1 1 and R 12 are identical or different and are independently hydrogen, (Ci-Cs) alkyl,
(C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C3-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Ci0)-Cycloalkenyl-(Ci-C8)-alkyl, COR13, S02R14, Heterocyclyl, (Ci-C8)- Alkoxycarbonyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkyl- aminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl-aminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- alkoxycarbonyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)- Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen, oder (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, (C 4 -Cio) -halocycloalkenyl, (Ci-C 8 ) - Alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -Alkylthio- (Ci-C 8 ) -alkyl, (Ci- C 8 ) -Haloalkylthio- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 4 -Ci 0 ) -cycloalkenyl- (Ci-C 8 ) -alkyl, COR 13 , S0 2 R 14 , heterocyclyl, (Ci-C 8 ) - alkoxycarbonyl, bis - [(Ci-C 8 ) -alkyl] aminocarbonyl- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -Alkyl- aminocarbonyl- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkyl-aminocarbonyl- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkoxycarbonyl, heteroaryl- (Ci-C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, (C 2 -C 8 ) -alkinyloxycarbonyl, heterocyclyl- (Ci-C 8 ) -alkyl, or
R1 1 und R12 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 1 1 and R 12 with the nitrogen atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, form partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R13 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C8)-Haloalkenyl, (C3-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Alkoxy- (Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryl, Aryl- (Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)- alkyl]aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkyl-aminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- alkyl-aminocarbonyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(C2-C6)-alkyl, (Ci-Cs)-Alkyl- amino-(C2-C6)-alkyl, Aryl-(Ci-C8)-alkyl-amino-(C2-C6)-alkyl, R14S-(Ci-C8)-alkyl, R14(0)S- (Ci-C8)-alkyl, R1402S-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl, R 13 for hydrogen, (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, ( C 4 -Cio) -halocycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -Alkoxy- (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci -C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) - (8 Ci-C) alkyl alkoxy- (Ci-C8) alkoxy, aryl, (Ci-C 8) alkyl aryl, aryl (Ci-C 8) alkoxy (Ci-C 8) alkyl, heteroaryl, (Ci-C 8) -alkyl heteroaryl, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 8) -alkyl, bis - [(Ci-C 8 ) - alkyl] aminocarbonyl- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkyl-aminocarbonyl- (Ci-C 8 ) -alkyl, aryl- (Ci -C 8 ) - alkyl-aminocarbonyl- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -alkyl] amino- (C 2 -C6) -alkyl, (Ci-Cs) -alkyl- a mino- (C 2 -C 6 ) -alkyl, aryl- (Ci-C 8 ) -alkyl-amino- (C 2 -C 6 ) -alkyl, R 14 S- (Ci-C 8 ) -alkyl, R 14 (0) S- (Ci-C 8 ) -alkyl, R 14 0 2 S- (Ci-C 8 ) -alkyl, hydroxycarbonyl- (Ci-C 8 ) -alkyl, heterocyclyl,
Heterocyclyl-(Ci-C8)-alkyl, Tris-[(Ci-C8)-Alkyl]silyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)- Alkyl](aryl)silyl(Ci-C8)-alkyl, [(Ci-C8)-Alkyl]-bis-(aiyl)süyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyloxy-(Ci-C8)-alkyl, (C3-C8)-Cycloalkylcarbonyloxy-(Ci-C8)-alkyl, Heterocyclyl (Ci-C 8 ) -alkyl, tris - [(Ci-C 8 ) -alkyl] silyl- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -alkyl] (aryl) silyl (Ci-C 8 ) -alkyl, [(Ci-C 8 ) -alkyl] -bis- (aiyl) süyl- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkylcarbonyloxy- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkylcarbonyloxy- (Ci-C 8 ) -alkyl,
Arylcarbonyloxy-(Ci-C8)-alkyl, Heteroarylcarbonyloxy-(Ci-C8)-alkyl, Heterocyclylcarbonyloxy-(Ci-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, Heteroaryloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl steht, Arylcarbonyloxy- (Ci-C 8 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 8 ) -alkyl, Heterocyclylcarbonyloxy- (Ci-C 8 ) -alkyl, aryloxy- (Ci-C 8 ) -alkyl, heteroaryloxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxycarbonyl,
R14 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C8)-Haloalkenyl, (C3-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl- (Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino, (Ci-C8)-Alkyl-amino, Aryl-(Ci-C8)- amino, Aryl-(Ci-C6)-alkyl-amino, Aryl-[(Ci-C8)-alkyl]amino; (C3-C8)-Cycloalkyl-amino, (C3- C8)-Cycloalkyl-[(Ci-C8)-alkyl]amino; N-Azetidinyl, N-Pyrrolidinyl, N-Piperidinyl. N- Morpholinyl, steht R 14 for hydrogen, (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, ( C 4 -Cio) -halocycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci -C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 4 -C 10 ) - Cycloalkenyl- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -alkyl] amino, (Ci-C 8 ) -alkyl-amino, aryl- (Ci-C 8 ) - amino, aryl (Ci-C 6 ) -alkyl-amino, aryl - [(Ci-C 8 ) -alkyl] amino; (C 3 -C 8) cycloalkyl-amino, (C 3 - C 8) cycloalkyl - [(Ci-C 8) alkyl] amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl. N-morpholinyl
und and
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen. X and Y independently represent O (oxygen) or S (sulfur).
Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin R1 für Wasserstoff, (Ci-C6)-Haloalkyl steht, Preferred subject matter of the invention are compounds of the general formula (I), in which R 1 is hydrogen, (Ci-C 6 ) -haloalkyl,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, (Ci-C6)-Alkoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-C 6 ) -alkoxy,
R3 für Wasserstoff, Halogen, (Ci-C6)-Alkoxy steht, R 3 represents hydrogen, halogen, (Ci-C 6 ) -alkoxy,
R4 für Halogen, Cyano, N02, C(0)NH2, C(S)NH2, (Ci-C6)-Haloalkyl, (C2-C6)-Alkinyl steht, R 4 represents halogen, cyano, N0 2 , C (0) NH 2 , C (S) NH 2 , (Ci-C 6 ) -haloalkyl, (C 2 -C 6 ) -alkynyl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, (C1-C7)- Haloalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkoxy stehen, R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (Ci-C 6 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (Ci-C 6 ) -alkoxy, (Ci-C 6 ) -Haloalkoxy stand,
G für unverzweigtes oder verzweigtes (Ci-C6)-Alkylen steht, G is unbranched or branched (Ci-C 6 ) -alkylene,
Q für einen Rest der Formel
Figure imgf000006_0001
steht, R8 für Wasserstoff, (Ci-C7)-Alkyl, (Ci-C7)-Haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl,Q for a remainder of the formula
Figure imgf000006_0001
stands, R 8 for hydrogen, (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl,
(C2-C7)-Alkinyl, (C2-C7)-Alkenyl, C(0)R13, C(0)0R13, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl steht, (C2-C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl, C (0) R 13 , C (0) 0R 13 , (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl stands,
R9 für Wasserstoff oder (Ci-G,)-Alkyl steht, R 9 represents hydrogen or (Ci-G,) - alkyl,
R10 für Cyano, N02, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, RnR12N-(Ci-C7)-alkyl, R130-(Ci-C7)-alkyl, Cyano-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyloxy- (Ci-C7)-alkyl, (C3-C7)-Cycloalkylcarbonyloxy-(Ci-C7)-alkyl, Arylcarbonyloxy-(Ci-C7)-alkyl, Heteroarylcarbonyloxy-(Ci-C7)-alkyl, Heterocyclylcarbonyloxy-(Ci-C7)-alkyl, OR13, NRnR12, SR14, S(0)R14, S02R14, R14S-(Ci-C7)-alkyl, R14(0)S-(Ci-C7)-alkyl, R1402S-(Ci-C7)-alkyl, Tris- [(Ci-C7)-Alkyl]silyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-Alkyl](aryl)silyl(Ci-C7)-alkyl, [(Ci-C7)-Alkyl]- bis-(aryl)silyl-(Ci-C7)-alkyl, Tris-[(Ci-C7)-Alkyl]silyl, Bis-hydroxyboryl-(Ci-C7)-alkyl, Bis- [(Ci-C7)-alkoxy]boryl-(Ci-C7)-alkyl, Tetramethyl- 1, 3, 2-Dioxaborolan-2-yl, Tetramethyl- 1,3,2- Dioxaborolan-2-yl-(Ci-C7)-alkyl, Nitro-(Ci-C7)-alkyl, C(0)R14, Bis-(Ci-C7)-alkoxymethyl, Bis- (Ci-C7)-alkoxymethyl-(Ci-C7)-alkyl steht, oder R 10 for cyano, N0 2 , heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, heterocyclyl, heterocyclyl- (Ci-C 7 ) -alkyl, R n R 12 N- (Ci-C 7 ) -alkyl, R 13 0- (Ci-C 7 ) -alkyl, cyano- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -Alkylcarbonyloxy- (Ci-C 7 ) -alkyl, (C3-C 7 ) -Cycloalkylcarbonyloxy- (Ci-C 7 ) -alkyl, arylcarbonyloxy- (Ci-C 7 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 7 ) -alkyl, heterocyclylcarbonyloxy- (Ci-C 7 ) -alkyl, OR 13 , NR n R 12 , SR 14 , S (0) R 14 , S0 2 R 14 , R 14 S- (Ci-C 7 ) -alkyl, R 14 (0) S- (Ci-C 7 ) -alkyl, R 14 0 2 S- (Ci-C 7 ) -alkyl, tris- [(Ci-C 7 ) -alkyl] silyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] (aryl) silyl (Ci -C 7 ) -alkyl, [(Ci-C 7 ) -alkyl] - bis (aryl) silyl- (Ci-C 7 ) -alkyl, tris - [(Ci-C 7 ) -alkyl] silyl, bis- hydroxyboryl- (Ci-C 7 ) -alkyl, bis- [(Ci-C 7 ) -alkoxy] boryl- (Ci-C 7 ) -alkyl, tetramethyl- 1, 3, 2-dioxaborolan-2-yl, tetramethyl- 1,3,2-Dioxaborolan-2-yl- (Ci-C 7 ) -alkyl, nitro- (Ci-C 7 ) -alkyl, C (0) R 14 , bis- (Ci-C 7 ) -alkoxymethyl, Bis- (Ci-C 7 ) -alkoxymethyl- (Ci-C 7 ) -alkyl, or
R8 und R10 mit dem Kohlenstoffatom, an das sie gebunden sind, ein vollständig gesättigtes oder R 8 and R 10 with the carbon atom to which they are attached are a fully saturated or
teilgesättigtes, und gegebenenfalls weiter substituiertes 3 bis 10-gliedriges monocyclisches oder bicyclisches Heterocyclyl bilden, partially saturated, and optionally further substituted 3 to 10-membered monocyclic or bicyclic heterocyclyl form,
R11 und R12 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl,R 11 and R 12 are identical or different and independently represent hydrogen, (Ci-C 7 ) -alkyl,
(C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C3-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, COR13, S02R14, Heterocyclyl, (Ci-C7)- Alkoxycarbonyl, Bis-[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkyl- aminocarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl-aminocarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)- alkoxycarbonyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)- Alkinyloxycarbonyl, Heterocyclyl-(Ci-C7)-alkyl stehen, oder (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C3- C 7 ) -haloalkynyl, (C3-Cio) -cycloalkyl, (C3-Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C 4 -Cio) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci -C 7 ) -alkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkylthio- (Ci-C 7 ) -alkyl, (Ci-C 7 ) - Haloalkylthio- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, (C3-C 7 ) -cycloalkyl- (Ci-C 7 ) -alkyl, (C 4 -Cio) -cycloalkenyl- (Ci-C 7 ) -alkyl, COR 13 , S0 2 R 14 , heterocyclyl , (Ci-C 7 ) - alkoxycarbonyl, bis - [(Ci-C 7 ) -alkyl] aminocarbonyl- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkyl- aminocarbonyl- (Ci-C 7 ) -alkyl, aryl- (Ci-C 7 ) -alkyl-aminocarbonyl- (Ci-C 7 ) -alkyl, aryl- (Ci-C 7 ) -alkoxycarbonyl, heteroaryl- (Ci-C 7 ) -alkoxycarbonyl, (C2- C 7 ) -alkenyloxycarbonyl, (C2-C 7 ) -alkinyloxycarbonyl, heterocyclyl- (Ci-C 7 ) -alkyl, or
R11 und R12 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 11 and R 12 with the nitrogen atom to which they are attached are fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R13 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C7)-Haloalkenyl, (C3-C7)-Haloalkinyl, (C3-Ci0)-Cycloalkyl, (C3-Cio)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkoxy- (Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Aryl, Aryl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkyl, (C4-Ci0)-Cycloalkenyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)- alkyl]aminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkyl-aminocarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)- alkyl-aminocarbonyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]amino-(C2-C5)-alkyl, (Ci-C7)-Alkyl- amino-(C2-C5)-alkyl, Aryl-(Ci-C7)-alkyl-amino-(C2-C5)-alkyl, R14S-(Ci-C7)-alkyl, R14(0)S- (Ci-C7)-alkyl, R1402S-(Ci-C7)-alkyl, Hydroxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl, form partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, R 13 for hydrogen, (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Ci 0 ) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4 -Cio) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy - (Ci-C 7 ) -haloalkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C7) alkoxy (Ci-C7) alkyl, aryl, aryl (Ci-C7) alkyl, aryl (Ci-C7) alkoxy (Ci-C7) alkyl , Heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (Ci-C 7 ) -alkyl, (C 4 -Ci 0 ) -cycloalkenyl- (Ci-C 7 ) - alkyl, bis - [(Ci-C 7 ) - alkyl] aminocarbonyl- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkyl-aminocarbonyl- (Ci-C 7 ) -alkyl, aryl- (Ci- C 7 ) -alkyl-aminocarbonyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] amino- (C 2 -C5) -alkyl, (Ci-C 7 ) -alkyl- a mino- (C 2 -C 5 ) -alkyl, aryl- (Ci-C 7 ) -alkyl-amino- (C 2 -C 5 ) -alkyl, R 14 S- (Ci-C 7 ) -alkyl, R 14 (0) S- (Ci-C 7 ) -alkyl, R 14 0 2 S- (Ci-C 7 ) -alkyl, hydroxycarbonyl- (Ci-C 7 ) -alkyl, heterocyclyl,
Heterocyclyl-(Ci-C7)-alkyl, Tris-[(Ci-C7)-Alkyl]silyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)- Alkyl](aryl)silyl(Ci-C7)-alkyl, [(Ci-C7)-Alkyl]-bis-(aryl)silyl-(Ci-C7)-alkyl, (Ci-C7)- Alkylcarbonyloxy-(Ci-C7)-alkyl, (C3-C7)-Cycloalkylcarbonyloxy-(Ci-C7)-alkyl, Heterocyclyl (Ci-C 7 ) -alkyl, tris - [(Ci-C 7 ) -alkyl] silyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] (aryl) silyl (Ci-C 7 ) -alkyl, [(Ci-C 7 ) -alkyl] -bis- (aryl) silyl- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkylcarbonyloxy- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkylcarbonyloxy- (Ci-C 7 ) -alkyl,
Arylcarbonyloxy-(Ci-C7)-alkyl, Heteroarylcarbonyloxy-(Ci-C7)-alkyl, Arylcarbonyloxy- (Ci-C 7 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 7 ) -alkyl,
Heterocyclylcarbonyloxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, Heteroaryloxy-(Ci-C7)-alkyl, , (Ci-C7)-Alkoxycarbonyl steht, Heterocyclylcarbonyloxy- (Ci-C 7 ) -alkyl, aryloxy- (Ci-C 7 ) -alkyl, heteroaryloxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxycarbonyl,
R14 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C7)-Haloalkenyl, (C3-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl- (Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]amino, (Ci-C7)-Alkyl-amino, Aryl-(Ci-C7)- amino, Aryl-(Ci-C4)-alkyl-amino, Aryl-[(Ci-C7)-alkyl]amino; (C3-C7)-Cycloalkyl-amino, (C3- C7)-Cycloalkyl-[(Ci-C7)-alkyl]amino; N-Azetidinyl, N-Pyrrolidinyl, N-Piperidinyl. N- Morpholinyl, steht R 14 for hydrogen, (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4- Cio) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, heterocyclyl- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (Ci-C 7 ) -alkyl, (C4- C10) - cycloalkenyl (Ci-C7) alkyl, bis - amino, - [(Ci-C 7) alkyl] amino, (Ci-C7) alkyl-amino, aryl (Ci-C 7) Aryl- (Ci-C4) -alkyl-amino, aryl- [(Ci-C 7 ) -alkyl] amino; (C 3 -C 7) cycloalkyl-amino, (C 3 - C 7) cycloalkyl, - [(Ci-C 7) alkyl] amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl. N-morpholinyl
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen. X and Y independently represent O (oxygen) or S (sulfur).
Besonders bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin R1 für Wasserstoff steht, R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, (Ci-Ce)-Alkoxy steht, Particularly preferred subject matter of the invention are compounds of the general formula (I) in which R 1 is hydrogen, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-Ce) -alkoxy,
R3 für Wasserstoff, Halogen, (G-G)-Alkoxy steht, R 3 represents hydrogen, halogen, (GG) -alkoxy,
R4 für Halogen, Cyano, NO2, C(0)NH2, C(S)NH2, (Ci-Ce)-Haloalkyl, (CA-C r,)- Alk i n\ l steht, R 4 represents halogen, cyano, NO2, C (0) NH 2 , C (S) NH2, (Ci-Ce) -haloalkyl, (CA-C r ,) - Alk in \ l,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (Ci-G,)-Alkyl. (G-G)- Haloalkyl, (G-G)-Alkoxy. (G-G)-Haloalkoxy stehen, R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (Ci-G,) - alkyl. (GG) - haloalkyl, (GG) -alkoxy. (GG) -haloalkoxy stand,
G für unverzweigtes oder verzweigtes (G-G)-Alkylen steht, G stands for unbranched or branched (G-G) -alkylene,
Q für einen Rest der Formel
Figure imgf000009_0001
steht, Q for a remainder of the formula
Figure imgf000009_0001
stands,
R8 für Wasserstoff, (Ci-G,)-Alkyl. (Ci-Ce)-Haloalkyl, Aryl, Aryl-(Ci-Ce)-alkyl, Heteroaryl, R 8 for hydrogen, (Ci-G,) - alkyl. (Ci-Ce) -haloalkyl, aryl, aryl- (Ci-Ce) -alkyl, heteroaryl,
(C2-C6)-Alkinyl, (C2-C6)-Alkenyl, C(0)R13, C(0)OR13, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl steht, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkenyl, C (0) R 13 , C (0) OR 13 , (Ci-C 6 ) -alkoxy- (Ci-C 6 ) - alkyl stands,
R9 für Wasserstoff oder (Ci-G)-Alkyl steht, R 9 represents hydrogen or (Ci-G) -alkyl,
R10 für Cyano, NO2, Heteroaryl, Heteroaryl-(Ci-Ce)-alkyl, Heterocyclyl, Heterocyclyl-(G-C6)-alkyl, RnR12N-(Ci-C6)-alkyl, R130-(G-C6)-alkyl, Cyano-(G-C6)-alkyl, (Ci-C6)-Alkylcarbonyloxy- (Ci-Ce)-alkyl, (C3-C6)-Cycloalkylcarbonyloxy-(Ci-C6)-alkyl, Arylcarbonyloxy-(Ci-C6)-alkyl, Heteroarylcarbonyloxy-(Ci-C6)-alkyl, Heterocyclylcarbonyloxy-(Ci-C6)-alkyl, OR13, NRnR12,R 10 for cyano, NO2, heteroaryl, heteroaryl- (Ci-Ce) -alkyl, heterocyclyl, heterocyclyl- (GC 6 ) -alkyl, R n R 12 N- (Ci-C 6 ) -alkyl, R 13 0- ( GC 6 ) -alkyl, cyano- (GC 6 ) -alkyl, (Ci-C 6 ) -Alkylcarbonyloxy- (Ci-Ce) -alkyl, (C3-C6) -Cycloalkylcarbonyloxy- (Ci-C6) -alkyl, Arylcarbonyloxy- (Ci-C 6 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 6 ) -alkyl, heterocyclylcarbonyloxy- (Ci-C 6 ) -alkyl, OR 13 , NR n R 12 ,
SR14, S(0)R14, S02R14, R14S-(Ci-C6)-alkyl, R14(0)S-(G-C6)-alkyl, R1402S-(Ci-C6)-alkyl, Tris-SR 14 , S (0) R 14 , S0 2 R 14 , R 14 S- (Ci-C 6 ) -alkyl, R 14 (0) S- (GC 6 ) -alkyl, R 14 0 2 S- (Ci -C 6 ) -alkyl, tris-
[(Ci-C6)-Alkyl]silyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)-Alkyl](aryl)silyl(Ci-C6)-alkyl, [(G-C6)-Alkyl]- bis-(aryl)silyl-(Ci-C6)-alkyl, Tris-[(Ci-C6)-Alkyl]silyl, Bis-hydroxyboryl-(Ci-C6)-alkyl, Bis- [(Ci-C6)-alkoxy]boryl-(Ci-C6)-alkyl, Tetramethyl- 1, 3, 2-Dioxaborolan-2-yl, Tetramethyl- 1,3,2- Dioxaborolan-2-yl-(Ci-C6)-alkyl, Nitro-(Ci-C(,)-alkyl. , C(0)R13, , Bis-(Ci-C6)-alkoxymethyl, Bis-(Ci-C6)-alkoxymethyl-(Ci-C6)-alkyl steht, [(Ci-C 6 ) -alkyl] silyl- (Ci-C 6 ) -alkyl, bis - [(Ci-C 6 ) -alkyl] (aryl) silyl (Ci-C 6 ) -alkyl, [(GC 6 ) -Alkyl] - bis- (aryl) silyl- (Ci-C 6 ) -alkyl, tris - [(Ci-C 6 ) -alkyl] silyl, bis-hydroxyboryl- (Ci-C 6 ) -alkyl, bis- [(Ci-C 6 ) -alkoxy] boryl- (Ci-C 6 ) -alkyl, tetramethyl- 1, 3, 2-dioxaborolan-2-yl, tetramethyl- 1,3,2-dioxaborolan-2-yl- ( Ci-C 6 ) -alkyl, nitro- (Ci-C ( ,) - alkyl., C (0) R 13 , bis- (Ci-C 6 ) -alkoxymethyl, bis- (Ci-C 6 ) -alkoxymethyl - (Ci-C 6 ) -alkyl,
R8 und R10 mit dem Kohlenstoffatom, an das sie gebunden sind, ein vollständig gesättigtes oder R 8 and R 10 with the carbon atom to which they are attached are a fully saturated or
teilgesättigtes, und gegebenenfalls weiter substituiertes 3 bis 10-gliedriges monocyclisches oder bicyclisches Heterocyclyl bilden, R1 1 und R12 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (C’i-G,)-Alkyl.partially saturated, and optionally further substituted 3 to 10-membered monocyclic or bicyclic heterocyclyl form, R 1 1 and R 12 are identical or different and are each independently hydrogen, (C 'i-G,) - alkyl.
(C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (G-Go)-Haloalkyl, (C2-C6)-Haloalkenyl, (C3-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (G-G)-AlkoxY-(G-G)-alkyl. (G-G)-HaloalkoxY-(G-G)-alkyl. (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, Aryl, Aryl-(G-G)-alkyl. Heteroaryl, Heteroaryl-(G-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-Cö)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, COR13, S02R14, Heterocyclyl, (Ci-C6)- Alkoxycarbonyl, Bis-[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (G-G)-Alkyl- aminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl-aminocarbonyl-(Ci-C6)-alkyl, Aryl-(G-G)- alkoxycarbonyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C(,)- Alkinyloxycarbonyl, Heterocyclyl-(Ci-C6)-alkyl stehen, oder (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl, (G-Go) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 3 -C 6 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, (C 4 -Cio) -halocycloalkenyl, (GG) -AlkoxY- ( GG) -alkyl. (GG) -haloalkoxy- (GG) -alkyl. (Ci-C 6 ) -Alkylthio- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -haloalkylthio- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) - haloalkyl, aryl, aryl- (GG) -alkyl. Alkyl heteroaryl, heteroaryl (G-C6) alkyl, (C 3 -C 6) -cycloalkyl- (Ci-C ö) alkyl, (C 4 -Cio) cycloalkenyl (C 6), COR 13 , S0 2 R 14 , heterocyclyl, (Ci-C 6 ) - alkoxycarbonyl, bis - [(Ci-C6) alkyl] aminocarbonyl (Ci-C6) alkyl, (GG) -alkyl aminocarbonyl (Ci- C6) -alkyl, aryl- (Ci-C6) -alkyl-aminocarbonyl- (Ci-C6) -alkyl, aryl- (GG) -alkoxycarbonyl, heteroaryl- (Ci-C6) -alkoxycarbonyl, (C 2 -C6) - Alkenyloxycarbonyl, (C 2 -C ( ,) -alkinyloxycarbonyl, heterocyclyl- (Ci-C6) -alkyl, or
R1 1 und R12 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 1 1 and R 12 with the nitrogen atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, form partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R13 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-G,)-Haloalkenyl. (C3-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (C i-C(,)-Alkoxy-(C i-C(,)- alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (G-C6)-Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Alkoxy- (Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, Aryl, Aryl- (Ci-Ce)-alkyl, Aryl-(Ci-C ,)-alkoxy-(Ci-C(,)-alkyl. Heteroaryl, Heteroaryl-(G-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)- alkyl]aminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-aminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-Ce)- alkyl-aminocarbonyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]amino-(C2-C4)-alkyl, (G-G)-Alkyl- amino-(C2-C4)-alkyl, Aryl-(Ci-C6)-alkyl-amino-(C2-C4)-alkyl, R14S-(Ci-C6)-alkyl, R14(0)S- (Ci-Ce)-alkyl, Rl402S-(Ci-C(,)-alkyl. Hydroxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl, R 13 for hydrogen, (Ci-C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -G,) - haloalkenyl. (C3-C6) -haloalkynyl, (C3-Cio) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, (C 4 -Cio) -halocycloalkenyl, (C iC ( ,) -Alkoxy- (C iC ( ,) - alkyl, (Ci-C 6 ) -haloalkoxy- (Ci-C 6 ) -alkyl, (GC 6 ) -alkoxy- (Ci-C 6 ) -haloalkyl, (Ci-C 6 ) -Alkoxy- (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkoxy- (Ci-C6) -alkoxy- (Ci-C6) -alkoxy- (Ci -C 6 ) -alkyl, (Ci-C6) -alkoxy- (Ci-C6) -alkoxy- (Ci-C6) -alkoxy- (Ci-C6) -alkoxy- (Ci-C6) -alkyl, aryl, aryl - (Ci-Ce) -alkyl, aryl- (Ci-C,) - alkoxy- (Ci-C ( ,) - alkyl.Heteroaryl, heteroaryl- (G-C6) -alkyl, (C 3 -C 6 ) - Cycloalkyl- (Ci-C 6 ) -alkyl, (C 4 -Cio) -cycloalkenyl- (Ci-C 6 ) -alkyl, bis- [(Ci-C 6 ) -alkyl] aminocarbonyl- (Ci-C6) -alkyl alkyl [(Ci-C 6) -, (Ci-C6) alkyl-aminocarbonyl (Ci-C6) alkyl, aryl (Ci-Ce) - alkyl-aminocarbonyl (Ci-C6) alkyl, bis ] amino- (C 2 -C 4 ) -alkyl, (GG) -alkyl-amino- (C 2 -C 4 ) -alkyl, aryl- (Ci-C6) -alkyl-amino- (C 2 -C 4 ) -alkyl, R 14 S- (Ci-C 6 ) -alkyl, R 14 (0) S- (Ci-Ce) -alkyl, R 14 0 2 S- (Ci-C ( ,) - alkyl. Hydroxycarbonyl- ( Ci-C6) -alkyl, heteroc yclyl,
Heterocyclyl-(Ci-C6)-alkyl, Tris-[(Ci-C6)-Alkyl]silyl-(Ci-C6)-alkyl, Bis-[(G-C6)- Alkyl](aryl)silyl(Ci-C6)-alkyl, [(Ci-C6)-Alkyl]-bis-(aryl)silyl-(Ci-C6)-alkyl, (Ci-Ce)- Alkylcarbonyloxy-(Ci-C6)-alkyl, (C3-C6)-Cycloalkylcarbonyloxy-(Ci-C6)-alkyl, Heterocyclyl (Ci-C 6 ) alkyl, tris - [(Ci-C6) alkyl] silyl (Ci-C 6 ) alkyl, bis - [(GC 6 ) alkyl] (aryl) silyl (Ci- C 6 ) -alkyl, [(Ci-C 6 ) -alkyl] -bis- (aryl) silyl- (Ci-C 6 ) -alkyl, (Ci-Ce) -alkylcarbonyloxy- (Ci-C6) -alkyl, ( C3-C6) -cycloalkylcarbonyloxy- (Ci-C6) -alkyl,
Arylcarbonyloxy-(Ci-C6)-alkyl, Heteroarylcarbonyloxy-(Ci-C6)-alkyl, Arylcarbonyloxy- (Ci-C6) -alkyl, heteroarylcarbonyloxy- (Ci-C6) -alkyl,
Heterocyclylcarbonyloxy-(Ci-C6)-alkyl, Aiyloxy-(Ci-C(,)-alkyl. Heteroaryloxy-(G-C6)-alkyl, , (Ci-C6)-Alkoxycarbonyl steht, Heterocyclylcarbonyloxy- (Ci-C6) -alkyl, Aiyloxy- (Ci-C ( ,) - alkyl. Heteroaryloxy- (G-C6) -alkyl,, (Ci-C6) -alkoxycarbonyl,
R14 für Wasserstoff, (G-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C(,)-Haloalkcnyl. (C3-C6)-Haloalkinyl, (C3-Go)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (CrG)-Alkoxy-(G-G)- alkyl, (CrG,)-Alkoxy-(Ci-G,)-haloalkyl. Aryl, Aryl-(G-G)-alk\i. Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C6)-alkyl, Bis-[(G-C6)-alkyl]amino, (G-C6)-Alkyl-amino, Aryl-(G-G)- amino, Aryl-(Ci-C2)-alkyl-amino, Aryl-[(G-C6)-alkyl]amino; (C3-C6)-Cycloalkyl-amino, (C3- C6)-Cycloalkyl-[(Ci-C6)-alkyl]amino; N-Azetidinyl, N-Pyrrolidinyl, N-Piperidinyl. N- Morpholinyl, steht R 14 for hydrogen, (GC 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl, (C 1 -C 10 ) -haloalkyl , (C 2 -C ( ,) - haloalkynyl. (C 3 -C 6 ) -haloalkynyl, (C3-Go) -cycloalkyl, (C 3 -C 10 ) - Halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4-Cio) -halocycloalkenyl, (CrG) -alkoxy- (GG) -alkyl, (CrG,) -alkoxy- (Ci-G,) -haloalkyl. Aryl, aryl (GG) alk \ i. Heteroaryl, heteroaryl- (Ci-C 6 ) -alkyl, heterocyclyl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C4-C10) -cycloalkenyl - (Ci-C 6 ) -alkyl, bis - [(GC 6 ) -alkyl] amino, (GC 6 ) -alkyl-amino, aryl- (GG) -amino, aryl- (Ci-C2) -alkyl-amino , Aryl - [(GC 6 ) alkyl] amino; (C 3 -C 6) cycloalkyl-amino, (C 3 - C 6) cycloalkyl, - [(Ci-C6) alkyl] amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl. N-morpholinyl
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen. X and Y independently represent O (oxygen) or S (sulfur).
Ganz besonders bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Very particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, Methoxy, Ethoxy, Prop-l-yloxy, But-1- yloxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-l-yloxy, but-1-yloxy,
R3 für Wasserstoff, Fluor, Chlor, Brom, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-1- yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1-Dimethyleth-l-yloxy steht, R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-l-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-l-yloxy, 1,1 -Dimethyleth-l-yloxy stands,
R4 für Fluor, Chlor, Brom, Cyano, NO2, C(0)NH2, C(S)NH2, Trifluormethyl, Difluormethyl, R 4 for fluorine, chlorine, bromine, cyano, NO2, C (0) NH 2 , C (S) NH2, trifluoromethyl, difluoromethyl,
Pentafluorethyl, Ethinyl, Propin- 1-yl, 1 -Butin- 1-yl, Pentin-l-yl, Hexin- 1-yl steht, Pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, Prop-l-yl, 1-Methylethyl, But-l-yl, 1 -Methylpropyl, 2-Methylpropyl, 1,1-Dimethylethyl, n- Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1,1-Dimethylpropyl, 1,2-Dimethylpropyl,R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl , 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,
2.2-Dimethylpropyl, 1-Ethylpropyl, n-Hexyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Di-methylbutyl, 2,2-Dimethylbutyl,2.2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2, 2-dimethylbutyl,
2.3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2- Trimethylpropyl, 1 -Ethyl- 1-methylpropyl, l-Ethyl-2-methylpropyl, Trifluormethyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, Trifluoromethyl,
Difluormethyl, Pentafluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Methoxy, Ethoxy, Prop-l- yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1-Dimethyleth-l- yloxy, Difluormethoxy, Trifluormethoxy, Pentafluorethoxy, 2,2-Difluorethoxy, 2,2,2- Trifluorethoxy stehen, G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Prop-l-yl)methylen, (Prop-2-yl)methylen, (But-l-yl)methylen, (But-2-yl)methylen, (Pent-l-yl)methylen, (Pent-2-yl)methylen, (Pent-3- yl)methylen, (Dimethyl)methylen, (Diethyl)methylen, Ethylen, n-Propylen, (l-Methyl)ethyl-l- en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1-en, 2-Methylpropyl-l-en, 3- Methylpropyl-l-en, 1,1-Dimethylethyl-l-en, 2,2-Dimethylethyl-l-en, 1-Ethylethyl-l-en, 2- Ethylethyl-l-en, l-(Prop-l-yl)ethyl-l-en, 2-(Prop-l-yl)ethyl-l-en, l-(Prop-2-yl)ethyl-l-en, 2- (Prop-2-yl)ethyl-l-en, 1,1,2-Trimethylethyl-l-en, 1,2,2-Trimethylethyl-l-en, 1, 1,2,2- Tetramethylethyl-l-en, n-Pentylen, 1-Methylbutyl-l-en, 2-Methylbutyl-l-en, 3-Methylbutyl-l- en, 4-Methylbutyl-l-en, 1,1-Dimethylpropyl-l-en, 2,2-Dimethylpropyl-l-en, 3,3- Dimethylpropyl-l-en, 1,2-Dimethylpropyl-l-en, 1,3-Dimethylpropyl-l-en, 1-Ethylpropyl-l-en, n-Hexylen, 1-Methylpentyl-l-en, 2-Methylpentyl-l-en, 3-Methylpentyl-l-en, 4-Methylpentyl-l- en, 1,1-Dimethylbutyl-l-en, 1,2-Dimethylbutyl-l-en, 1,3-Di-methylbutyl-l-en, 2,2- Dimethylbutyl-l-en, 2,3 -Dimethylbutyl- 1-en, 3,3-Dimethylbutyl-l-en, 1-Ethylbutyl-l-en, 2- Ethylbutyl-l-en, 1,1,2-Trimethylpropyl-l-en, 1,2,2-Trimethylpropyl-l-en, 1-Ethyl-l- methylpropyl-l-en, l-Ethyl-2-methylpropyl-l-en steht, Difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-l-yloxy, prop-2-yloxy, but-l-yloxy, but-2-yloxy, 2-methylprop- l-yloxy, 1,1-dimethyleth-l-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, G for methylene, (methyl) methylene, (ethyl) methylene, (prop-l-yl) methylene, (prop-2-yl) methylene, (but-l-yl) methylene, (but-2-yl) methylene, (Pent-l-yl) methylene, (pent-2-yl) methylene, (pent-3-yl) methylene, (dimethyl) methylene, (diethyl) methylene, ethylene, n-propylene, (l-methyl) ethyl 1-ene, (2-methyl) ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1 -en, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1- (prop-1-yl) ethyl-1-ene, 2- (prop-l -yl) ethyl-1-ene, 1- (prop-2-yl) ethyl-1-ene, 2- (prop-2-yl) ethyl-1-ene, 1,1,2-trimethylethyl-1-ene 1,2,2-trimethylethyl-1-ene, 1, 1,2,2-tetramethylethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl -lene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1 -en, 1,3-dimethylpropyl-1-en, 1-ethylpropyl-1-ene, n-hexylene, 1-methylpentyl-1-ene, 2-methylpentyl-1-ene, 3-methylpentyl-1-ene, 4 -Methylpentyl-l-en, 1,1-dimethyl l-butyl-ene, 1,2-dimethylbutyl-l-ene, 1,3-dimethylbutyl-l-ene, 2,2-dimethylbutyl-l-ene, 2,3-dimethylbutyl-1-ene, 3, 3-dimethylbutyl-1-en, 1-ethylbutyl-1-en, 2-ethylbutyl-1-en, 1,1,2-trimethylpropyl-1-en, 1,2,2-trimethylpropyl-1-en, 1- Ethyl-l-methylpropyl-l-ene, l-ethyl-2-methylpropyl-l-ene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen und X and Y independently of one another represent O (oxygen) or S (sulfur) and
Q für eine der nachfolgend spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q-57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q-180, Q-182 bis Q-185, Q-193 bis Q-195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bis Q-440 steht: Q for one of the following specifically named groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q-195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 says:
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Im Speziellen bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Wasserstoff, Fluor, Chlor, Brom, Methoxy steht, R4 für Fluor, Chlor, Brom, Cyano, NO2, C(0)NH2, C(S)NH2, Trifluormethyl, Ethinyl, Propin- 1-yl steht, R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy, R 4 represents fluorine, chlorine, bromine, cyano, NO 2 , C (0) NH 2 , C (S) NH 2 , trifluoromethyl, ethynyl, propyne 1- yl stands,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy stehen, G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Dimethyl)methylen, Ethylen, n-Propylen, (l-Methyl)ethyl-l-en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1-en, 2 -Methylpropyl -R 5 , R 6 and R 7 independently represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, G for methylene, (methyl) methylene, (ethyl) methylene, (dimethyl) methylene, ethylene, n-propylene, (1-methyl) ethyl-1-ene, (2-methyl) ethyl-1-ene, n-butylene , 1-methylpropyl-1-en, 2-methylpropyl -
1-en, 3 -Methylpropyl- 1-en, 1,1-Dimethylethyl-l-en, 2,2-Dimethylethyl-l-en, 1-Ethylethyl-l-en,1-en, 3-methylpropyl-1-en, 1,1-dimethylethyl-l-ene, 2,2-dimethylethyl-l-ene, 1-ethylethyl-l-ene,
2-Ethylethyl-l-en, l-(Prop-l-yl)ethyl-l-en, 2-(Prop-l-yl)ethyl-l-en, l-(Prop-2-yl)ethyl-l-en, 2- (Prop-2-yl)ethyl-l-en, n-Pentylen, 1-Methylbutyl-l-en, 2-Methylbutyl-l-en, 3-Methylbutyl-l- en, 4-Methylbutyl-l-en, 1,1-Dimethylpropyl-l-en, 2,2-Dimethylpropyl-l-en, 3,3- Dimethylpropyl-l-en, 1,2-Dimethylpropyl-l-en, 1,3-Dimethylpropyl-l-en, 1-Ethylpropyl-l-en, n-Hexylen, steht, 2-ethylethyl-1-ene, 1- (prop-1-yl) ethyl-1-ene, 2- (prop-1-yl) ethyl-1-ene, 1- (prop-2-yl) ethyl-1 -en, 2- (prop-2-yl) ethyl-l-ene, n-pentylene, 1-methylbutyl-l-ene, 2-methylbutyl-l-ene, 3-methylbutyl-l-ene, 4-methylbutyl- l-ene, 1,1-dimethylpropyl-l-ene, 2,2-dimethylpropyl-l-ene, 3,3-dimethylpropyl-l-ene, 1,2-dimethylpropyl-l-ene, 1,3-dimethylpropyl- l-ene, 1-ethylpropyl-l-ene, n-hexylene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen und X and Y independently of one another represent O (oxygen) or S (sulfur) and
Q für eine der oben spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q-57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q-180, Q-182 bis Q-185, Q-193 bis Q- 195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bis Q-440 steht. Q for one of the above-mentioned groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q- 195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 stands.
Im ganz Speziellen bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin The very particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Fluor steht, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2, C(0)NH2, C(S)NH2 steht, R 4 represents chlorine, bromine, cyano, NO2, C (0) NH 2 , C (S) NH2,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl,
Trifluormethyl, Methoxy, Trifluormethoxy stehen, Trifluoromethyl, methoxy, trifluoromethoxy,
G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Dimethyl)methylen, Ethylen, n-Propylen, (l-Methyl)ethyl-l-en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1-en, 2 -Methylpropyl - 1-en, 3 -Methylpropyl- 1-en, n-Pentylen, n-Hexylen steht, G for methylene, (methyl) methylene, (ethyl) methylene, (dimethyl) methylene, ethylene, n-propylene, (1-methyl) ethyl-1-ene, (2-methyl) ethyl-1-ene, n-butylene , 1-methylpropyl-1-en, 2-methylpropyl-1-en, 3-methylpropyl-1-en, n-pentylene, n-hexylene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen und X and Y independently represent O (oxygen) or S (sulfur) and
Q für eine der oben spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q-57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q-180, Q-182 bis Q-185, Q-193 bis Q- 195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bis Q-440 steht. Q for one of the above-mentioned groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q- 195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 stands.
Im besonders Speziellen bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Particularly particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Fluor steht, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2 steht, R 4 stands for chlorine, bromine, cyano, NO2,
R5 für Wasserstoff steht, R 5 represents hydrogen,
R6 für Wasserstoff, Fluor, Chlor, Brom steht, R 6 represents hydrogen, fluorine, chlorine, bromine,
R7 für Wasserstoff steht, R 7 represents hydrogen,
G für Methylen steht, G stands for methylene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen und X and Y independently of one another represent O (oxygen) or S (sulfur) and
Q für eine der oben spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q-57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q-180, Q-182 bis Q-185, Q-193 bis Q- 195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bis Q-440 steht. Im ganz besonders Speziellen bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Q for one of the above-mentioned groupings Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q- 195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q- 440 stands. The very particularly particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Fluor steht, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2 steht, R 4 stands for chlorine, bromine, cyano, NO2,
R5 für Wasserstoff steht, R 5 represents hydrogen,
R6 für Wasserstoff, Fluor steht, R 6 represents hydrogen, fluorine,
R7 für Wasserstoff steht, R 7 represents hydrogen,
G für Methylen steht, G stands for methylene,
X für O (Sauerstoff) oder S (Schwefel) steht, X stands for O (oxygen) or S (sulfur),
Y für O (Sauerstoff) steht, und Y stands for O (oxygen), and
Q für eine der oben spezifisch genannten Gruppierungen Q-l bis Q-35, Q-41, Q-42, Q-71 bis Q-80, Q- 115, Q-120, Q-152 bis Q-155, Q-166 bis Q-170, Q-176 bis Q-206, Q-211 bis Q-214, Q-280 bis Q-358, Q-362 bis Q-370, Q-405, Q-408 bis Q-410, Q-421 bis Q-429 steht. Q for one of the above-mentioned groupings Ql to Q-35, Q-41, Q-42, Q-71 to Q-80, Q-115, Q-120, Q-152 to Q-155, Q-166 to Q-170, Q-176 to Q-206, Q-211 to Q-214, Q-280 to Q-358, Q-362 to Q-370, Q-405, Q-408 to Q-410, Q- 421 to Q-429.
Im äußerst Speziellen bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Particularly preferred subject matter of the invention are compounds of the general formula (I), in which
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R3 für Fluor steht, R 2 represents fluorine, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2 steht, R 4 stands for chlorine, bromine, cyano, NO2,
R5 für Wasserstoff steht, R 5 represents hydrogen,
R6 für Wasserstoff, Fluor steht, R 6 represents hydrogen, fluorine,
R7 für Wasserstoff steht, R 7 represents hydrogen,
G für Methylen steht, G stands for methylene,
X für O (Sauerstoff) oder S (Schwefel) steht, X stands for O (oxygen) or S (sulfur),
Y für O (Sauerstoff) steht, und Y stands for O (oxygen), and
Q für eine der oben spezifisch genannten Gruppierungen Q-l, Q-2, Q-6, Q-23, Q-26, Q-31, Q-41, Q-71, Q-72, Q-l 15, Q-154, Q-166, Q-176, Q-201, Q-211, Q-280, Q-286, Q-288, Q-301, Q-350, Q-366, Q- 367, Q-368, Q-405, Q-421, Q-422, Q-424 steht. Q for one of the above-mentioned groupings Ql, Q-2, Q-6, Q-23, Q-26, Q-31, Q-41, Q-71, Q-72, Ql 15, Q-154, Q -166, Q-176, Q-201, Q-211, Q-280, Q-286, Q-288, Q-301, Q-350, Q-366, Q-367, Q-368, Q-405 , Q-421, Q-422, Q-424.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können The radical definitions given above in general or in areas of preference apply both to the end products of the general formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can
untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. can be combined as desired with one another, i.e. also between the specified preferred ranges.
Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfmdungsgemäße Verbindungen der genannten allgemeinen Formel (I) oder deren Salze bzw. deren erfmdungsgemäße Verwendung von besonderem Interesse, worin einzelne Reste eine der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen kombiniert auftreten. Mainly for the reasons of the higher herbicidal activity, better selectivity and / or better producibility, compounds of the general formula (I) according to the invention or their salts or their use according to the invention, in which individual radicals are one of those already mentioned or mentioned below, are of particular interest have preferred meanings, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
Wenn die Verbindungen durch WasserstoffVerschiebung Tautomere bilden können, welche strukturell formal nicht durch die allgemeine Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorhegen, wobei beide Formen durch die Definition der Verbindung der allgemeinen Formel (I) umfasst werden. If the compounds can form tautomers by hydrogen shift which structurally formally would not be covered by the general formula (I), then these tautomers are nevertheless included in the definition of the compounds of the general formula (I) according to the invention, if not a particular tautomer is under consideration. For example, many carbonyl compounds can exist both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von der allgemeinen Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. The compounds of the general formula (I) can be present as stereoisomers, depending on the nature and linkage of the substituents. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during the preparation by customary separation methods. The chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale to produce test samples for biological testing. Likewise, stereoisomers can be selectively produced by using stereoselective reactions using optically active starting materials and / or auxiliaries. The invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not indicated with their specific stereoform, and to mixtures thereof.
Sofern die Verbindungen als Feststoffe erhalten werden, kann die Reinigung auch durch If the compounds are obtained as solids, the purification can also be done by
Umkristallisieren oder Digerieren erfolgen. Sofern einzelne Verbindungen (I) nicht auf den nachstehend beschriebenen Wegen zufriedenstellend zugänglich sind, können sie durch Derivatisierung anderer Verbindungen (I) hergestellt werden. Recrystallization or digestion take place. If individual compounds (I) are not satisfactorily accessible in the ways described below, they can be prepared by derivatizing other compounds (I).
Als Isolierungs-, Reinigungs- und Stereoisomerenauftrennungsverfahren von Verbindungen der allgemeinen Formel (I) kommen Methoden in Frage, die dem Fachmann aus analogen Fällen allgemein bekannt sind, z.B. durch physikalische Verfahren wie Kristallisation, Chromatographieverfahren, vor allem Säulenchromatographie und HPFC (Hochdruckflüssigchromatographie), Destillation, gegebenenfalls unter reduziertem Druck, Extraktion und andere Verfahren, können gegebenfalls verbleibende Gemische in der Regel durch chromatographische Trennung, z.B. an chiralen Festphasen, getrennt werden. Für präparative Mengen oder im industriellen Maßstab kommen Verfahren in Frage wie Kristallisation, z.B. diastereomerer Salze, die aus den Diastereomerengemischen mit optisch aktiven Säuren und gegebenenfalls bei vorhandenen sauren Gruppen mit optisch aktiven Basen erhalten werden können. Suitable isolation, purification and stereoisomer separation processes for compounds of the general formula (I) are methods which are generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatography processes, especially column chromatography and HPFC (high pressure liquid chromatography), distillation , optionally under reduced pressure, extraction and other processes, any remaining mixtures can usually be separated by chromatographic separation, for example on chiral solid phases. For preparative quantities or on an industrial scale, processes such as crystallization, e.g. diastereomeric salts, which can be obtained from the diastereomeric mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable.
Im Hinblick auf die erfmdungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: Sofern nicht anders definiert, gilt generell für die Bezeichnung von chemischen Gruppen, dass die Anbindung an das Gerüst bzw. den Rest des Moleküls über das zuletzt genannte Strukturelement der betreffenden chemischen Gruppe erfolgt, d.h. beispielsweise im Falle von (C2-Cs)-Alkenyloxy über das Sauerstoffatom, und im Falle von Heterocyclyl-(Ci-C8)-alkyl oder (Ci-C6)-Alkoxy-(Ci-Cö)-alkoxy- (Ci-Ce)-alkyl jeweils über das C-Atom der Alkylgruppe. With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and have in particular the meanings explained below: Unless otherwise defined, the general rule for the designation of chemical groups is that the connection to the framework or the rest of the molecule takes place via the last-mentioned structural element of the chemical group in question, ie, in the case of (C2-Cs) -alkenyloxy, via the oxygen atom, and in the case of heterocyclyl (Ci-C 8 ) -alkyl or (Ci-C 6 ) -alkoxy- (Ci-C ö ) -alkoxy- (Ci-Ce) -alkyl in each case via the C atom of Alkyl group.
Erfmdungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, “alkylsulfonyl” - on its own or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, z.B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfonyl wie Methylsulfonyl, Ethyl- sulfonyl, Propylsulfonyl, 1-Methylethylsulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2 -Methyl - propylsulfonyl, 1,1-Dimethylethylsulfonyl, Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutyl- sulfonyl, 3-Methylbutylsulfonyl, 1,1-Dimethylpropylsulfonyl, 1,2-Dimethylpropylsulfonyl, 2,2-Di- methylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1,1-Dimethylbutylsulfonyl, 1,2-Di- methylbutylsulfonyl, 1,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1,1,2-Trimethylpropylsulfonyl,Carbon atoms, e.g. (but not limited to) (Ci-C 6 ) -alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 1-methylpentylsulfonyl 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1-ethylsulphonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,
1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl . 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.
Erfmdungsgemäß steht "Heteroarylsulfonyl" für gegebenenfalls substituiertes Pyridylsulfonyl, According to the invention "Heteroarylsulfonyl" stands for optionally substituted pyridylsulfonyl,
Pyrimidinylsulfonyl, Pyrazinylsulfonyl oder gegebenenfalls substituiertes polycyclisches Pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic
Heteroarylsulfonyl, hier insbesondere gegebenenfalls substituiertes Chinolinylsulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, Iod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. Heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfmdungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "alkylthio" - on its own or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8 or 1 to 6
Kohlenstoffatomen, wie (Ci-Cio)-, (Ci-G,)- oder (Ci-C- -Alkylthio, z.B. (aber nicht beschränkt auf) (Ci- C6)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methylpropylthio, 1,1-Dimethylethylthio, Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3- Methylbutylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1- Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutyl- thio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Tri- methylpropylthio, 1,2,2-Trimethylpropylthio, 1 -Ethyl- 1-methylpropylthio und l-Ethyl-2-methyl- propylthio. „Alkenylthio“ bedeutet erfmdungsgemäßt ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Carbon atoms, such as (Ci-Cio) -, (Ci-G,) - or (Ci-C- alkylthio, e.g. (but not limited to) (Ci- C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1- Methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and l-ethyl 2-methyl-propylthio. According to the invention, “alkenylthio” means an alkenyl radical bonded via a sulfur atom, alkynylthio means an alkynyl radical bonded via a sulfur atom, cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom and cycloalkenylthio means a via one
Schwefelatom gebundenen Cycloalkenylrest. Cycloalkenyl radical bonded to sulfur atom.
.Alkylsulfinyl (Alkyl-S(=0)-)“, soweit nicht an anderer Stelle anders definiert steht erfindungsgemäß für Alkylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (Ci-Ce)- oder (C1-C4)- Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butylsulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1,1-Dimethylethylsulfinyl, Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3- Methylbutylsulfinyl, 1,1-Dimethylpropylsulfinyl, 1,2-Dimethylpropylsulfinyl, 2,2-Di- methylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethyl- butylsulfinyl, 1,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1,1,2-Trimethylpropylsulfinyl, 1,2,2- Trimethylpropylsulfinyl, 1-Ethyl-l-methylpropylsulfinyl und l-Ethyl-2-methylpropylsulfmyl. .Alkylsulfinyl (alkyl-S (= 0) -) ", unless otherwise defined elsewhere, stands according to the invention for alkyl radicals that are bonded to the skeleton via -S (= 0) -, such as (Ci-Cio) -, ( Ci-Ce) - or (C1-C4) - alkylsulfinyl, e.g. B. (but not limited to) (Ci-C 6 ) -Alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2 -Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methyl-methyl-pentylsulfinyl, 4-methyl-pentylsulfinyl , 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1 , 2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfmyl.
Analog sind„Alkenylsulfinyl“ und„Alkinylsulfinyl“, erfmdungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (CVG,)- oder (C2-C4)- Alkenylsulfinyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfinyl. Analogously, “alkenylsulfinyl” and “alkynylsulfinyl” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= 0) -, such as (C2-C10) -, (CVG,) - or (C2 -C4) -alkenylsulfinyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfinyl.
Analog sind„Alkenylsulfonyl“ und„Alkinylsulfonyl“ erfmdungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)2- an das Gerüst gebunden sind, wie (C2-C10)-, (CVG,)- oder (C2-C4)- Alkenylsulfonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfonyl. Analogously, “alkenylsulfonyl” and “alkynylsulfonyl” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= 0) 2 -, such as (C2-C10) -, (CVG,) - or (C2 -C4) -alkenylsulfonyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfonyl.
„Alkoxy“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (G-G)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2- Methylpropoxy, 1,1-Dimethylethoxy, Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1,1- Dimethylpropoxy, 1,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1-Ethylpropoxy, Hexoxy, 1- Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1,1-Dimethylbutoxy, 1,2-Di- methylbutoxy, 1,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1- Ethylbutoxy, 2-Ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-Ethyl-l-methyl- propoxy und l-Ethyl-2-methylpropoxy. Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenoxy bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinoxy. „Cycloalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. “Alkoxy” means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (GG) -alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methyl-propoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy denotes an alkenyl radical bonded via an oxygen atom, alkynyloxy denotes an alkynyl radical bonded via an oxygen atom such as (C2-C10) -, (C 2 -C 6 ) - or (C2-C4) -alkenoxy or (C3-C10) -, (C3-C6) or (C3-C4) alkinoxy. “Cycloalkyloxy” means a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
..Alkylcarbonyl (Alkyl-C(=0)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (Ci-Ce)- oder (C1-C4)- Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der ..Alkylcarbonyl (alkyl-C (= 0) -), unless otherwise defined, stands according to the invention for alkyl radicals which are bonded to the skeleton via -C (= 0) -, such as (Ci-Cio) -, (Ci-Ce) - or (C 1 -C 4 ) - alkylcarbonyl. The number of carbon atoms relates to the alkyl radical in the
Alkylcarbonylgruppe . Alkylcarbonyl group.
Analog stehen„Alkenylcarbonyl“ und„Alkinylcarbonyl“, soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyl bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkinylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonylgruppe. Analogously, “alkenylcarbonyl” and “alkynylcarbonyl”, unless otherwise defined, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -C (= 0) -, such as (C 2 -C 10 ) - , (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenylcarbonyl or (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkynylcarbonyl. The number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynyl carbonyl group.
„Alkoxycarbonyl (Alkyl-0-C(=0)-)“, soweit nicht an anderer Stelle anders definiert: Alkylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C1-C10)-, (C|-C(,)- oder (Ci-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe. Analog stehen „Alkenyloxycarbonyl“ und„Alkinyloxycarbonyl“, soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenyloxycarbonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)- Alkinyloxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alken- bzw. Alkinyloxycarbonylgruppe. "Alkoxycarbonyl (alkyl-0-C (= 0) -)", unless otherwise defined: alkyl radicals that are attached to the structure via -0-C (= 0) -, such as (C 1 -C 10 ) -, (C | -C ( ,) - or (Ci-C 4 ) -alkoxycarbonyl. The number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group. "Alkenyloxycarbonyl" and "alkynyloxycarbonyl" are analogous if not Defined differently elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -0-C (= 0) -, such as (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -Alkenyloxycarbonyl or (C 3 -C 10 ) -, (C 3 -C6) - or (C 3 -C 4 ) - alkynyloxycarbonyl, the number of carbon atoms referring to the alkenyl - or alkynyl radical in the alkene or alkynyloxycarbonyl group.
Der Begriff„Alkylcarbonyloxy“ (Alkyl-C(=0)-0-) steht erfindungsgemäß, soweit nicht an anderer Stelle anders definiert, für Alkylreste, die über eine Carbonyloxygruppe (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C1-C10)-, (Ci-G,)- oder (Ci-C4)-Alkylcarbonyloxy. Die Anzahl der C- Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonyloxygruppe. The term “alkylcarbonyloxy” (alkyl-C (= 0) -0-) stands according to the invention, unless otherwise defined, for alkyl radicals connected to the oxygen via a carbonyloxy group (-C (= 0) -0-) the skeleton are bound, such as (C 1 -C 10 ) -, (Ci-G,) - or (Ci-C 4 ) -Alkylcarbonyloxy. The number of C atoms relates to the alkyl radical in the alkylcarbonyloxy group.
Analog sind„Alkenylcarbonyloxy“ und„Alkinylcarbonyloxy“ erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyloxy bzw. (C2-C10)-, (CA-C ,)- oder (C2-C4)-Alkinylcarbonyloxy. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonyloxygruppe . Analogously, “alkenylcarbonyloxy” and “alkynylcarbonyloxy” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (= 0) -0-) with the oxygen, such as (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenylcarbonyloxy or (C 2 -C 10 ) -, (CA-C,) - or (C 2 -C 4 ) -alkynylcarbonyloxy. The number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
In Kurzformen wie z.B. C(0)R13, C(0)OR13, OC(0)NRnR12, oder C(0)NRnR12 steht die in Klammem aufgeführte Kurzform O für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes Sauerstoffatom. In Kurzformen wie z.B. OC(S)OR13, OC(S)SR14, OC(S)NRnR12, steht die in Klammem aufgeführte Kurzform S für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes In short forms such as C (0) R 13 , C (0) OR 13 , OC (0) NR n R 12 , or C (0) NR n R 12 , the short form O listed in brackets stands for a via a double bond to the adjacent carbon atom bonded oxygen atom. In short forms such as OC (S) OR 13 , OC (S) SR 14 , OC (S) NR n R 12 , the short form S listed in brackets stands for a double bond to the adjacent carbon atom
Schwefelatom. Sulfur atom.
Der Begriff„Aryl“ bedeutet ein gegebenenfalls substituiertes mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C-Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl. The term “aryl” means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
Vom Begriff„gegebenenfalls substituiertes Aryl“ sind auch mehrcyclische Systeme, wie The term “optionally substituted aryl” also includes multicyclic systems such as
Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl“ in der Regel auch von dem Begriff „gegebenenfalls substituiertes Phenyl“ umfasst. Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris- [alkyl]silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris-[alkyl]silylalkinyl, Arylalkinyl, Tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, wherein the binding site is on the aromatic system. From a systematic point of view, “aryl” is usually also included in the term “optionally substituted phenyl”. Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkyl, alkylthio, haloalkyl Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris- [alkyl] silyl, bis- [alkyl] arylsilyl, bis- [alkyl] alkylsilyl, tris- [alkyl] silylalkynyl, arylalkynyl, arylalkynyl
Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino,
Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino,
Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Alkylaminocarbonyl, cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
Arylalkoxy Arylalkoxy
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring
(=carbocycbscher Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfasst, wie beispielsweise 8-Aza-bicyclo[3.2.1]octanyl, 8-Aza-bicyclo[2.2.2]octanyl oder 1-Aza- bicyclo[2.2.1]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch (= carbocyclic ring in which at least one carbon atom has been replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and can be unsubstituted or substituted, wherein the binding site is located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, multicyclic systems are also included, such as, for example, 8-aza-bicyclo [3.2.1] octanyl, 8-aza-bicyclo [2.2.2] octanyl or 1-aza-bicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl are also
spirocyclische Systeme umfasst, wie beispielsweise l-Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1, 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei Includes spirocyclic systems such as l-oxa-5-aza-spiro [2.3] hexyl. Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms heterocyclic ring, preferably from the group N, O, and S, but not two
Sauerstoffatome direkt benachbart sein sollen, wie beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1- oder 2- oder 3-Pyrrolidinyl, 3,4-Dihydro-2H-pyrrol-2- oder 3-yl, 2,3-Dihydro-lH-pyrrol-Oxygen atoms should be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3- Dihydro-1H-pyrrole-
1- oder 2- oder 3- oder 4- oder 5-yl; 2,5-Dihydro-lH-pyrrol-l- oder 2- oder 3-yl, 1- oder 2- oder 3- oder 4-Piperidinyl; 2,3,4,5-Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; 1, 2,3,6- Tetrahydropyridin-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2,3,4-Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,4-Dihydropyridin-l- oder 2- oder 3- oder 4-yl; 2,3-Dihydropyridin-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1, 2,3,6-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridin-1- or 2- or 3- or 4-yl; 2,3-dihydropyridine
2- oder 3- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl, 1- oder 2- oder 3- oder 4-Azepanyl; 2,3,4,5-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2, 3,6,7- Tetrahydro-lH-azepin-1- oder 2- oder 3- oder 4-yl; 3,4,5,6-Tetrahydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-lH-azepin-l- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-lH-azepin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridin-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepine-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,6,7-tetrahydro-1H-azepin-1- or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1H-azepin-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-azepine-
1- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- yl; 2,3-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,4-Dihydro-2H-azepin-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1H-azepin-1- or -2- or 3- or 4-yl; 2,3-dihydro-1H-azepine-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-dihydro-2H-azepine-
2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 5,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-3H-azepine
2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 1H-Azepin-1- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl, 2- oder 3-Oxolanyl (= 2- oder 3- Tetrahydrofüranyl); 2,3-Dihydrofüran-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofüran-2- oder 3-yl, 2- oder 3- oder 4-Oxanyl (= 2- oder 3- oder 4-Tetrahydropyranyl); 3,4-Dihydro-2H-pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-pyran-2- oder 3-oder 4- oder 5- oder 6-yl; 2H-Pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Pyran-2- oder 3- oder 4-yl, 2- oder 3- oder 4-Oxepanyl; 2, 3,4,5- Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oder2- or 3- or 4- or 5- or 6- or 7-yl; 1H-azepine-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2, 3,4,5-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydrooxepine-2 or 3 or
4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepine-2 or
3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder3- or 4- or 5- or 6- or 7-yl; 4,5-dihydrooxepin-2- or 3- or 4-yl; 2,5-dihydrooxepine-2 or
3- oder 4- oder 5- oder 6- oder 7-yl; Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2- oder 3- Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H-thiopyran-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder3- or 4- or 5- or 6- or 7-yl; Oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-2- or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or
5- oder 6-yl; 3,6-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring- Heterocyclen sind beispielsweise 1- oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1- oder 2- oder 3-Azetidinyl,5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-ring and 4-ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
2- oder 3-Oxetanyl, 2- oder 3-Thietanyl, l,3-Dioxetan-2-yl. Weitere Beispiele für“Heterocyclyl“ sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit zwei Heteroatomen aus der Gruppe N,2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group N,
O und S, wie beispielsweise 1- oder 2- oder 3- oder 4-Pyrazolidinyl; 4,5-Dihydro-3H-pyrazol- 3- oder 4- oder 5-yl; 4,5-Dihydro-lH-pyrazol-l- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-lH-pyrazol-l- oder 2- oderO and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1- or 2- or
3- oder 4- oder 5-yl; 1- oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-lH-imidazol-l- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; 4,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; Hexahydropyridazin-1- oder 2- oder 3- oder 4-yl; 1,2,3,4-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2,3,6-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,4,5,6-Tetrahydropyridazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3,4,5,6-Tetrahydropyridazin-3- oder 4- oder 5-yl; 4,5-Dihydropyridazin-3- oder 4-yl; 3,4-Dihydropyridazin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydropyridazin-3- oder 4-yl; 1,6-Dihydropyriazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-Dihydro-1H-imidazole-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; Hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyriazin-1- or 3- or 4- or 5- or 6-yl;
Hexahydropyrimidin-1- oder 2- oder 3- oder 4-yl; 1,4,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1,2,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1,2, 3, 4- Tetrahydropyrimidin-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,6-Dihydropyrimidin-l- oder 2- oderHexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2, 3, 4- tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidine-1- or 2- or
4- oder 5- oder 6-yl; 1,2-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine
2- oder 4- oder 5-yl; 4,5-Dihydropyrimidin- 4- oder 5- oder 6-yl; 1,4-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; 1,2,3,6-Tetrahydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; 1,2,3,4-Tetrahydropyrazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2-Dihydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; 1,4-Dihydropyrazin-l- oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-1- or 2- or 3-yl; 2,3-dihydropyrazine-2- or
3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; l,3-Dioxolan-2- oder 4- oder 5-yl; l,3-Dioxol-2- oder 4-yl; l,3-Dioxan-2- oder 4- oder 5-yl; 4H-l,3-Dioxin-2- oder 4- oder 5- oder 6-yl; l,4-Dioxan-2- oder 3- oder 5- oder 6-yl; 2,3-Dihydro-l,4-dioxin-2- oder 3- oder 5- oder 6-yl; l,4-Dioxin-2- oder 3-yl;3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; 1,3-dioxolan-2- or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxan-2- or 4- or 5-yl; 4H-1,3-dioxin-2- or 4- or 5- or 6-yl; 1,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl;
1.2-Dithiolan-3- oder 4-yl; 3H-l,2-Dithiol-3- oder 4- oder 5-yl; l,3-Dithiolan-2- oder 4-yl; 1,3-Dithiol- 2- oder 4-yl; l,2-Dithian-3- oder 4-yl; 3,4-Dihydro-l,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro
1.2-dithiin-3- oder 4-yl; l,2-Dithiin-3- oder 4-yl; l,3-Dithian-2- oder 4- oder 5-yl; 4H-l,3-Dithiin-2- oder 4- oder 5- oder 6-yl; Isoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1,3-dithiin-2- or 4- or 5- or 6-yl; Isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazole-2 or 3 or
4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder 4- oder 5-yl;4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl;
1.3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-oxazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; l,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-l,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; l,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-
1.3-oxazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl; 2H-
1.3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-l,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-l,4-oxazin-2- oder 3-yl; l,2-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,3,4,5-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,2- oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,3- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-1,3-oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-oxazin-2- or 4- or 5- or 6-yl; Morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2 or 3 or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepine-2 or 3 or
4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,5,6,7-Tetrahydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-l,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,3-oxazepine-2 or 3 or 4 or 5 or
6- oder 7-yl; 2,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,3-oxazepin- 2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7- Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; l,4-Oxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2, 3,4,7- Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,4-oxazepin-6- or 7-yl; 2,5-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,4,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepine
2- oder 3- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,4- oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or
7-yl; 2,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,4-oxazepin-2- oder7-yl; 2,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2 or
3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 6,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; l,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; Isothiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisothiazol-2- oder 3- oder 4- oder 5- yl; 2,5-Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisothiazol-3- oder 4- oder 5-yl; 1,3- Thiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-thiazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; l,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,3-thiazin-2- oder 4- oder3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; Isothiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5- yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-thiazine-2 or 4 or
5- oder 6-yl; 5,6-Dihydro-4H-l,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl. Weitere Beispiele für“Heterocyclyl“ sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise l,4,2-Dioxazolidin-2- oder 3- oder 5-yl; l,4,2-Dioxazol-3- oder 5-yl; l,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-l,4,2- dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-7H-l,4,2- Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H-l,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden aufgeführt: 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1,2,4-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l, 4,2-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:
Figure imgf000036_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000038_0001
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, The heterocycles listed above are preferred, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, tris-alkylsilylalkynyl, nitro, amino, cyano, haloalkoxy,
Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy,
Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heteroaryloxy, Bis- alkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bis-alkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl (alkyl) amino, aminocarbon
Alkylaminocarbonyl, Bis-alkylaminocarbonyl, Cycloalkylaminocarbonyl, Alkylaminocarbonyl, bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
Hydroxycarbonylalkylaminocarbonyl, Alkoxycarbonylalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl,
Arylalkoxycarbonylalkylaminocarbonyl substituiert. Arylalkoxycarbonylalkylaminocarbonyl substituted.
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein. If a base is substituted “by one or more radicals” from a list of radicals (= group) or a generically defined group of radicals, this includes the simultaneous substitution by several identical and / or structurally different radicals.
Handelt es sich es sich um einen teilweise oder vollständig gesättigten Stickstoff-Heterocyclus, so kann dieser sowohl über Kohlenstoff als auch über den Stickstoff mit dem Rest des Moleküls verknüpft sein. If it is a partially or fully saturated nitrogen heterocycle, it can be linked to the rest of the molecule both via carbon and via nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Oxogruppe als Substituent an einem Ring- C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(0)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(0)-Gruppen sind jeweils beide Enantiomere umfasst. Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, additionally also oxo and thioxo. The oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams. The oxo group can also occur on the hetero-ring atoms, which can exist in different oxidation states, e.g. with N and S, and then form, for example, the divalent groups N (O), S (O) (also SO) and S (0) 2 ( also briefly SO2) im heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
Erfmdungsgemäß steht der Ausdruck„Heteroaryl“ für heteroaromatische Verbindungen, d. h. According to the invention, the term “heteroaryl” stands for heteroaromatic compounds; H.
vollständig ungesättigte aromatische heterocyclische Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Erfmdungsgemäße Heteroaryle sind beispielsweise lH-Pyrrol-l-yl; lH-Pyrrol-2-yl; lH-Pyrrol-completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; lH pyrrole
3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-Imidazol-l-yl; lH-Imidazol-2-yl; lH-Imidazol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; lH-imidazole-
4-yl; lH-Imidazol-5-yl; lH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, 4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-l-yl, lH-l, 2,3-triazol-4-yl, lH-l, 2,3-triazol-5-yl, 2H-l, 2,3-triazol-2-yl, 2H-l, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl, 1H-1, 2,4- Triazol-3-yl, 4H-l, 2,4-triazol-4-yl, l, 2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, l, 3,4- Oxadiazol-2-yl, l, 2,3-oxadiazol-4-yl, l, 2,3-oxadiazol-5-yl, l, 2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, Pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl,
Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, l,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, 1,2,4-Triazolonyl und 1,2,4-Diazepinyl, 2H-l,2,3,4-Tetrazol-5-yl, lH-l,2,3,4-Tetrazol-5-yl, l,2,3,4-Oxatriazol-5-yl, l,2,3,4-Thiatriazol-5-yl, l,2,3,5-Oxatriazol-4-yl, l,2,3,5-Thiatriazol-4-yl. Die erfmdungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, l, 3,5-triazin-2-yl, l, 2,4-triazin-3-yl, l, 2,4-triazin-5-yl, l, 2,4-triazin-6-yl, l, 2,3-triazin-4-yl, l, 2,3-triazin-5-yl, 1,2, 4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2 -yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl , 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H-1,3,4 -Tetrazol-5-yl, l H-l, 2,3,4-tetrazol-5-yl, l, 2,3,4-oxatriazol-5-yl, l, 2,3,4-thiatriazol-5-yl , 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention can also be substituted by one or more, identical or different radicals. Are two adjacent
Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten. Carbon atoms are part of another aromatic ring, so it is a matter of fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatic.
Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5- yl, Chinolin-6-yl, Chinolin-7-yl, Chinolin- 8 -yl); Isochinoline (z. B. Isochinolin- 1-yl, Isochinolin-3-yl, Isochinolin-4-yl, Isochinolin-5-yl, Isochinolin-6-yl, Isochinolin-7-yl, Isochinolin-8-yl); Chinoxalin; Chinazolin; Cinnolin; 1,5-Naphthyridin; 1,6-Naphthyridin; 1,7-Naphthyridin; 1,8-Naphthyridin; 2,6- Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe lH-Indol-l-yl, lH-Indol-2-yl, lH-Indol-3-yl, lH-Indol-4-yl, lH-Indol-5-yl, 1H- Indol-6-yl, lH-Indol-7-yl, l-Benzofuran-2-yl, l-Benzofüran-3-yl, l-Benzofüran-4-yl, l-Benzofuran-5- yl, l-Benzofüran-6-yl, l-Benzofüran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5-yl, l-Benzothiophen-6-yl, l-Benzothiophen-7-yl, lH-Indazol-For example, quinolines (for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl) are preferred ); Isoquinolines (e.g. isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); Quinoxaline; Quinazoline; Cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; Phthalazine; Pyridopyrazines; Pyridopyrimidines; Pyridopyridazine; Pteridines; Pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzofused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran 5- yl, l-Benzofüran-6-yl, l-Benzofüran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5- yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, lH-indazole-
1 -yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol- 2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H- Isoindol-2-yl, 2H-Isoindol-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, lH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, l,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, l,2-Benzisothiazol-7-yl. 1 -yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2- yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, lH-benzimidazol-l-yl, lH-benzimidazol-2-yl, lH-benzimidazol-4-yl, 1H- Benzimidazol-5-yl, 1H-Benzimidazol-6-yl, 1H-Benzimidazol-7-yl, 1,3-Benzoxazol-2-yl, 1,3-Benzoxazol-4-yl, 1,3-Benzoxazol-5- yl, l, 3-benzoxazol-6-yl, l, 3-benzoxazol-7-yl, l, 3-benzthiazol-2-yl, l, 3-benzothiazol-4-yl, l, 3-benzthiazol-5- yl, l, 3-benzthiazol-6-yl, l, 3-benzthiazol-7-yl, 1,2-benzisoxazol-3-yl, l, 2-benzisoxazol-4-yl, l, 2-benzisoxazol-5- yl, l, 2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, l, 2-benzisothiazol-3-yl, l, 2-benzisothiazol-4-yl, l, 2-benzisothiazol-5- yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl.
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder Iod. Wird die The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. Will the
Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder Iodatom. When the term is used for a radical, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.
Erfmdungsgemäß bedeutet„Alkyl“ einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist und im letzteren Falle als „substituiertes Alkyl“ bezeichnet wird. Bevorzugte Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder Iod. Die Vorsilbe„Bis“ schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Ethyl (Methyl). According to the invention, “alkyl” means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted and in the latter case is referred to as “substituted alkyl”. Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred. The prefix “bis” also includes the combination of different alkyl radicals, e.g. B. methyl (ethyl) or ethyl (methyl).
„Haloalkyl“, ,,-alkenyl“ und ,,-alkinyl“ bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl "Haloalkyl", "- alkenyl" and "- alkynyl" mean partially or completely substituted alkyl, alkenyl or alkynyl, e.g. monohaloalkyl, by identical or different halogen atoms
(= Monohalogenalkyl) wie z. B. CH2CH2CI, C^CTTBr, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z.(= Monohaloalkyl) such as e.g. B. CH 2 CH 2 CI, C 1-4 CTTBr, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as e.g.
B. CC13, CCIF2, CFC12,CF2CC1F2, CF2CCIFCF3; Polyhaloalkyl wie z. B. CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. B. CC1 3, CCIF 2, CFC1 2 , CF 2 CC1F 2, CF 2 CCIFCF 3 ; Polyhaloalkyl such as e.g. B. CHFC1 CH 2, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3; The term perhaloalkyl also includes the term perfluoroalkyl.
„Teilfluoriertes Alkyl“ bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der einfach oder mehrfach durch Fluor substituiert ist, wobei sich die entsprechenden Fluoratome als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 “Partially fluorinated alkyl” means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, where the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as. B. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
„Teilfluoriertes Haloalkyl“ bedeutet einen geradkettigen oder verzweigten, gesättigten “Partially fluorinated haloalkyl” means a straight or branched chain, saturated one
Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor oder Brom, Iod. Die entsprechenden Halogenatome können sich dabei als Hydrocarbon which is substituted by different halogen atoms with at least one fluorine atom, all other halogen atoms optionally present being selected from the group fluorine, chlorine or bromine, iodine. The corresponding halogen atoms can be
Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden. Teilfluoriertes Haloalkyl schließt auch die vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein. Substituents on one or more different carbon atoms of the straight or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the complete substitution of the straight-chain or branched chain by halogen with the participation of at least a fluorine atom.
„Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und 0CH2CH2C1; Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. “Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 C1; The same applies to haloalkenyl and other halogen-substituted radicals.
Der hier beispielhaft genannte Ausdruck "(Ci-C -Alkyl" bedeutet eine Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der The expression "(Ci-C-alkyl" mentioned here by way of example) means an abbreviation for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to
Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1-Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(Ci-C6)-Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. Range for carbon atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals with a larger specified range of carbon atoms, e.g. B. "(Ci-C 6 ) -Alkyl", accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1-Methylhexyl und 1,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including those in composite radicals, are preferably the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or, in the case of unsaturated groups, with 2 to 6 carbon atoms. Alkyl radicals, including those in the composite radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Preference is given to radicals with a double bond or
Dreifachbindung . Triple bond.
Der Begriff„Alkenyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkenyl” also includes, in particular, straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1,3-Butadienyl und 1,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1,2-Propadienyl), 1,2-Butadienyl und 1,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (C2-G, (-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl, 1-Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl- 1-propenyl, 2-Methyl-l-propenyl, 1 -Methyl -2 -propenyl, 2-Methyl-2-propenyl, 1- Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl- 1-butenyl, 2-Methyl-l-butenyl, 3 -Methyl- 1- butenyl, 1 -Methyl -2 -butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3- butenyl, 3-Methyl-3-butenyl, 1,1-Dimethyl -2 -propenyl, 1,2-Dimethyl- 1-propenyl, l,2-Dimethyl-2- propenyl, 1 -Ethyl- 1-propenyl, 1 -Ethyl -2 -propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl- 1-pentenyl, 2-Methyl-l-pentenyl, 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3- pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl -4-pentenyl, 2- Methyl-4-pentenyl, 3 -Methyl -4-pentenyl, 4-Methyl-4-pentenyl, l,l-Dimethyl-2-butenyl, 1, 1-Dimethyl- 3-butenyl, 1,2-Dimethyl-l-butenyl, l,2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, 1,3-Dimethyl-l- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l-butenyl, 3,3-Dimethyl-2- butenyl, 1-Ethyl-l-butenyl, l-Ethyl-2-butenyl, l-Ethyl-3-butenyl, 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, l, l,2-Trimethyl-2-propenyl, l-Ethyl-l-methyl-2-propenyl, l-Ethyl-2-methyl-l- propenyl und l-Ethyl-2-methyl-2-propenyl. Hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, e.g. (but not limited to) (C 2 -G, (-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1- Butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl -2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl -2-butenyl, 2-methyl-2-butenyl, 3- Methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl -2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-Dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl -2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl 1-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, 1- methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2- pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl l -4-pentenyl, 2- Methyl-4-pentenyl, 3-methyl -4-pentenyl, 4-methyl-4-pentenyl, l, l-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-l- butenyl, l, 2-dimethyl-2-butenyl, l, 2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l, 3-dimethyl-2-butenyl, l, 3-dimethyl-3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-l-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2- butenyl, 2-ethyl-3-butenyl, l, l, 2-trimethyl-2-propenyl, l-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl 2-methyl-2-propenyl.
Der Begriff„Alkinyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkynyl” also includes, in particular, straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Hydrocarbon radicals with more than one triple bond or with one or more
Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1,3-Butatrienyl bzw. 3-Penten-l-in-l-yl. (C2-C6)-Alkinyl bedeutet z.B. Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl -2 -propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl -2- butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3 -Methyl- 1-butinyl, l,l-Dimethyl-2-propinyl, 1-Ethyl- 2 -propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl -2 -pentinyl, l-Methyl-3- pentinyl, 1 -Methyl -4-pentinyl, 2-Methyl-3 -pentinyl, 2-Methyl-4-pentinyl, 3 -Methyl- 1 -pentinyl, 3- Methyl-4-pentinyl, 4-Methyl-l -pentinyl, 4-Methyl -2 -pentinyl, l,l-Di-methyl-2-butinyl, l, l-Dimethyl-3- butinyl, l,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3, 3 -Dimethyl- 1-butinyl, l-Ethyl-2-butinyl, 1- Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-l-methyl -2 -propinyl. Triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C2-C6) -Alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl -2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl , 4-pentynyl, 1-methyl -2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl - 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl -2-pentynyl, 1-methyl-3-pentynyl, 1-methyl -4-pentynyl, 2 -Methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2 -pentynyl, 1,1 -Di-methyl-2-butynyl, l, l-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, l -Ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl -2-propynyl.
Der Begriff„Cycloalkyl“ bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, das gegebenenfalls weiter substituiert ist, bevorzugt durch Wasserstoff, Alkyl, Alkoxy, Cyano, Nitro, Alkylthio, Haloalkylthio, Halogen, Alkenyl, Alkinyl, Haloalkyl, AMino, Alkylamino, Bisalkylamino, Alkocycarbonyl, The term “cycloalkyl” means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, AMino, alkylamino, bisalkylamino, alkocycarbonyl,
Hydroxycarbonyl, Arylalkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am Cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, with substituents with a double bond on the
Cy cloalkylrest, z. B. eine Alkylidengruppe wie Methybden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfasst, wie beispielsweise Bicyclo [1.1.0]butan- 1 -yl, Bicyclo [1.1.0]butan-2-yl, Bicyclo [2.1.0]pentan- 1 -yl, Bicyclo [1.1.1 ]pentan- 1 - yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1.0]pentan-5-yl, Bicyclo [2. l . l]hexyl, Bicyclo[2.2.1]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-l-yl und Adamantan-2-yl, aber auch Systeme wie z. B. I,l'-Bi(cy clopropyl)- 1-yl, l,l'-Bi(cyclopropyl)-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Cycloalkyl radical, e.g. B. an alkylidene group such as methybdenum are included. In the case of optionally substituted cycloalkyl, multicyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 -yl , Bicyclo [1.1.1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2. l. l] hexyl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonane-2- yl, Adamantan-l-yl and Adamantan-2-yl, but also systems such as z. B. 1,1'-Bi (cyclopropyl) -1-yl, 1,1'-Bi (cyclopropyl) -2-yl. The term “(C3-C7) -cycloalkyl” means an abbreviation for cycloalkyl with three to seven
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfasst, wie beispielsweise Spiro[2.2]pent-l-yl, Spiro[2.3]hex-l-yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl,Carbon atoms according to the range given for C atoms. In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
Spiro [3.3]hept- 1 -yl, Spiro [3.3]hept-2-yl . Spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
„Cycloalkenyl“ bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, 1,3-Cyclohexadienyl oder 1,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. "Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 carbon atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, with substituents with a double bond on the cycloalkenyl radical, e.g. B. an alkylidene group such as methylidene are included. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.
Der Begriff„Alkyliden“, z. B. auch in der Form (Ci-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Alkyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H- Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B. =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 oder =C(C2H5)-C2H5 Cycloalkyliden bedeutet ein The term "alkylidene", e.g. B. also in the form (Ci-Cio) -Alkyliden, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond. Naturally, only positions on the base body at which two H atoms can be replaced by the double bond are possible as a binding site for alkylidene; Remnants are e.g. B. = CH 2 , = CH-CH 3 , = C (CH 3 ) -CH 3 , = C (CH 3 ) -C2H 5 or = C (C2H 5 ) -C2H 5 means cycloalkylidene
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. carbocyclic radical that is linked via a double bond.
Der Begriff„Alkylen“, z. B. auch in der Form (Ci-Cs)-Alkylen, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der an zwei Positionen an weitere Gruppen gebunden ist. The term "alkylene", e.g. B. also in the form (Ci-Cs) -alkylene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded to other groups in two positions.
„Cycloalkylalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylalkylrest und „Arylalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Arylalkylrest. “Cycloalkylalkyloxy” means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
„Alkoxyalkyl“ steht für einen über eine Alkylgruppe gebundenen Alkoxyrest und„Alkoxyalkoxy“ bedeutet einen über ein Sauerstoffatom gebundenen Alkoxyalkylrest, z.B. (aber nicht beschränkt auf) Methoxymethoxy, Methoxyethoxy, Ethoxyethoxy, Methoxy-n-propyloxy. “Alkoxyalkyl” stands for an alkoxy radical bonded via an alkyl group and “alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
„Alkylthioalkyl“ steht für einen über eine Alkylgruppe gebundenen Alkylthiorest und “Alkylthioalkyl” stands for an alkylthio radical bonded via an alkyl group and
„Alkylthioalkylthio“ bedeutet einen über ein Sauerstoffatom gebundenen Alkylthioalkylrest. “Alkylthioalkylthio” means an alkylthioalkyl radical bonded via an oxygen atom.
„Arylalkoxyalkyl“ steht für einen über eine Alkylgruppe gebundenen Aryloxyrest und “Arylalkoxyalkyl” stands for an aryloxy radical bonded via an alkyl group and
„Heteroaryloxyalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heteroaryloxyrest. “Heteroaryloxyalkyl” means a heteroaryloxy radical bonded via an alkyl group.
„Haloalkoxyalkyl“ steht für einen gebundenen Haloalkoxyrest und„Haloalkylthioalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Haloalkylthiorest. ..Arylalkyl steht für einen über eine Alkylgruppe gebundenen Arylrest,„Heteroarylalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heterocyclylrest. “Haloalkoxyalkyl” stands for a bonded haloalkoxy radical and “haloalkylthioalkyl” means a haloalkylthio radical bonded via an alkyl group. ..Arylalkyl stands for an aryl radical bonded via an alkyl group, “Heteroarylalkyl” means a heteroaryl radical bonded via an alkyl group, and “Heterocyclylalkyl” means a heterocyclyl radical bonded via an alkyl group.
„Cy cloalkylalkyl“ steht für einen über eine Alkylgruppe gebundenen Cy cloalkylrest, z. B. (aber nicht beschränkt auf) Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, 1- Cyclopropyleth-l-yl, 2-Cyclopropyleth-l-yl, 1-Cyclopropylprop-l-yl, 3-Cyclopropylprop-l-yl. “Cy cloalkylalkyl” stands for a cycloalkyl radical bonded via an alkyl group, e.g. B. (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.
„Arylalkenyl“ steht für einen über eine Alkenylgruppe gebundenen Arylrest,„Heteroarylalkenyl“ bedeutet einen über eine Alkenylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkenyl“ bedeutet einen über eine Alkenylgruppe gebundenen Heterocyclylrest. “Arylalkenyl” stands for an aryl radical bonded via an alkenyl group, “Heteroarylalkenyl” means a heteroaryl radical bonded via an alkenyl group, and “Heterocyclylalkenyl” means a heterocyclyl radical bonded via an alkenyl group.
„Arylalkinyl“ steht für einen über eine Alkinylgruppe gebundenen Arylrest,„Heteroarylalkinyl“ bedeutet einen über eine Alkinylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkinyl“ bedeutet einen über eine Alkinylgruppe gebundenen Heterocyclylrest. “Arylalkynyl” stands for an aryl radical bonded via an alkynyl group, “Heteroarylalkynyl” means a heteroaryl radical bonded via an alkynyl group, and “Heterocyclylalkynyl” means a heterocyclyl radical bonded via an alkynyl group.
Erfmdungsgemäß steht "Haloalkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Halogenalkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "haloalkylthio" - on its own or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably with 1 to 8 or 1 to 6
Kohlenstoffatomen, wie (Ci-Cs)-, (CrG,)- oder (Ci-C- -Haloalkylthio, z.B. (aber nicht beschränkt auf) Trifluormethylthio, Pentafluorethylthio, Difluormethyl, 2,2-Difluoreth-l-ylthio, 2,2,2-Difluoreth-l- ylthio, 3,3,3-prop-l-ylthio. Carbon atoms such as (Ci-Cs) -, (CrG,) - or (Ci-C- haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-l-ylthio, 2,2 , 2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
„Halocycloalkyl“ und„Halocycloalkenyl“ bedeuten durch gleiche oder verschiedene Halogenatome, wie z. B. F, CI und Br, oder durch Haloalkyl, wie z. B. Trifluormethyl oder Difluormethyl teilweise oder vollständig substituiertes Cy cloalkyl oder Cycloalkenyl , z.B. 1-Fluorcycloprop-l-yl, 2-Fluorcycloprop- 1-yl, 2,2-Difluorcycloprop-l-yl, 1-Fluorcyclobut-l-yl, 1-Trifluormethylcycloprop-l-yl, 2- Trifluormethylcycloprop- 1 -yl, 1 -Chlor-cycloprop- 1 -yl, 2-Chlorcycloprop- 1 -yl, 2,2-Dichlorcycloprop- 1 - yl, 3,3-Difluorcyclobutyl, "Halocycloalkyl" and "Halocycloalkenyl" mean by the same or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, for example 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1 -Trifluoromethylcycloprop-1-yl, 2- trifluoromethylcycloprop-1 -yl, 1-chlorocycloprop-1 -yl, 2-chlorocycloprop-1 -yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl,
Erfmdungsgemäß steht "Trialkylsilyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Si-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, “trialkylsilyl” - on its own or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8 or 1 to 6
Kohlenstoffatomen, wie Tri-[(Ci-C8)-, (Ci-G,)- oder (Ci-C4)-alkyl]silyl, z.B. (aber nicht beschränkt auf) Trimethylsilyl, Triethylsilyl, Tri-(n-propyl)silyl, Tri-(iso-propyl)silyl, Tri-(n-butyl)silyl, Tri-(1- methylprop-l-yl)silyl, Tri-(2-methylprop-l-yl)silyl, Tri(l,l-Dimethyleth-l-yl)silyl, Tri (2, 2- Dimethyleth- 1 -yl) silyl . „Trialkylsilylalkinyl“ steht für einen über eine Alkinylgruppe gebundenen Trialkylsilylrest. Carbon atoms such as tri - [(Ci-C 8 ) -, (Ci-G,) - or (Ci-C4) -alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (iso-propyl) silyl, tri- (n-butyl) silyl, tri- (1-methylprop-l-yl) silyl, tri- (2-methylprop-l-yl) silyl, tri (l, 1-dimethyleth-1-yl) silyl, tri (2,2-dimethyleth-1 -yl) silyl. “Trialkylsilylalkynyl” stands for a trialkylsilyl radical bonded via an alkynyl group.
Synthese von substituierten N-Phenyluracilen der allgemeinen Formel (I). Synthesis of substituted N-phenyluracils of the general formula (I).
Die erfmdungsgemäßen substituierten N-Phenyluracile der allgemeinen Formel (I) können ausgehend von bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren heteroaromatischen Aminen und von entsprechend substituierten Hydroxyestem aus. Die Gruppierungen G, Q, R1, R2, R3, R4, R5, R6, R7, X und Y der allgemeinen Formel (I) haben in den nachfolgenden Schemata die zuvor definierten The substituted N-phenyluracils of the general formula (I) according to the invention can be prepared on the basis of known processes. The synthetic routes used and investigated are based on commercially available or easily prepared heteroaromatic amines and correspondingly substituted hydroxy esters. The groupings G, Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X and Y of the general formula (I) have those defined above in the following schemes
Bedeutungen, sofern nicht beispielhafte, aber nicht einschränkende, Definitionen erfolgen. Als erstes Schlüsselintermediat für die Synthese der erfmdungsgemäßen Verbindungen der allgemeinen Formel (Ia), bei denen X für Schwefel (S) und Y für Sauerstoff (O) steht, wird ein gegebenenfalls weiter substituiertes Mercaptophenyl-lH-pyrimidin-2,4-dion hergestellt. Beispielhaft, aber nicht Meanings, unless exemplary, but not restrictive, definitions are given. An optionally further substituted mercaptophenyl-1H-pyrimidine-2,4-dione is prepared as the first key intermediate for the synthesis of the compounds of the general formula (Ia) according to the invention in which X stands for sulfur (S) and Y for oxygen (O) . Exemplary, but not
einschränkend, wird dies an der Synthese von 3-(4-Chlor-2-fluor-5-mercaptophenyl)-l-methyl-6- trifluormethyl-lH-pyrimidin-2,4-dion (Ha) gezeigt (Schema 1). Dazu wird ein geeignetes substituiertes Anilin, beispielhaft, aber nicht einschränkend, 2-Fluor-4-Chloranilin, mit einem geeigneten Reagenz (z. B. Triphosgen) in einem geeigneten polar-aprotischen Lösemittel (z. B. Dichlormethan) in das entsprechende Isocyanat überführt, das im nächsten Schritt durch Umsetzung mit einem geeigneten Aminoacrylsäureester unter Verwendung einer geeigneten Base (z. B. Natriumhydrid oder Kalium -tert- butylat) in einem geeigneten polar-aprotischen Lösemittel (z. B. N,N-Dimethylformamid) in das entsprechende gegebenenfalls weiter substituierte Pyrimidin-2,4-dion, beispielhaft, aber nicht einschränkend, 3-(4-Chlor-2-fluorphenyl)-l-methyl-6-trifluormethyl-lH-pyrimidin-2,4-dion, überführt (Schema 1). Durch nachfolgende Sulfochlorierung mit einem geeigneten Reagenz (z. B. restrictively, this is shown by the synthesis of 3- (4-chloro-2-fluoro-5-mercaptophenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Ha) (Scheme 1). For this purpose, a suitable substituted aniline, for example, but not limiting, 2-fluoro-4-chloroaniline, is converted into the corresponding isocyanate with a suitable reagent (e.g. triphosgene) in a suitable polar aprotic solvent (e.g. dichloromethane) transferred, which in the next step by reaction with a suitable amino acrylic acid ester using a suitable base (e.g. sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g. N, N-dimethylformamide) in the corresponding optionally further substituted pyrimidine-2,4-dione, for example, but not limiting, 3- (4-chloro-2-fluorophenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione, transferred ( Scheme 1). Subsequent sulfochlorination with a suitable reagent (e.g.
Chlorsulfonsäure) und anschließende Reduktion mit einem geeigneten Reduktionsmittel (z. B. Zn in EtOH und HCl, Zinn(II)chlorid-Hydrat oder Triphenylphosphin) kann das gewünschte weiter substituierte Mercaptophenyl-lH-pyrimidin-2,4-dion, beispielhaft, aber nicht einschränkend, 3-(4-Chlor- 2-fluor-5-mercaptophenyl)- 1 -methyl-6-trifluormethyl- lH-pyrimidin-2,4-dion (Ha), hergestellt werden (vgl. KR1345394; EP1122244; EP408382; WO 2003/029226; W02010/038953; US2011/0224083; KR2011/110420). Im nachfolgenden Schema 1 stehen R1 beispielhaft, aber nicht einschränkend für Wasserstoff, R2 und R3 beispielhaft, aber nicht einschränkend für Fluor, R4 beispielhaft, aber nicht einschränkend für Chlor und X beispielhaft, aber nicht einschränkend für Schwefel. Schema 1. Chlorosulphonic acid) and subsequent reduction with a suitable reducing agent (e.g. Zn in EtOH and HCl, tin (II) chloride hydrate or triphenylphosphine), the desired further substituted mercaptophenyl-1H-pyrimidine-2,4-dione, for example, but non-limiting, 3- (4-chloro-2-fluoro-5-mercaptophenyl) -1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Ha), can be prepared (cf. KR1345394; EP1122244; EP408382 ; WO 2003/029226; W02010 / 038953; US2011 / 0224083; KR2011 / 110420). In Scheme 1 below, R 1 is exemplary but not limiting for hydrogen, R 2 and R 3 are exemplary but not limiting for fluorine, R 4 is exemplary but not limiting for chlorine and X is exemplary, but not limiting for sulfur. Scheme 1.
Die in Schema 1 beschriebene Synthese des Schlüsselintermediats (Ha) kann auch auf die Herstellung ähnlicher Intermediate angewendet werden, z. B. 3-(4-Chlor-2-fluor-5-mercaptophenyl)-l-methyl -5,6- ditrifluormethyl-lH-pyrimidin-2,4-dion (Ilb). Hierbei wird beispielhaft, aber nicht einschränkend Ethyl- 4,4,4-trifluor-3-oxo-2-(trifluormethyl)butanoat (vgl. Journal of Fluorine Chemistry (2016), 181, 1-6) als Ausgangsmaterial verwendet. Im nachfolgenden Schema 1 stehen R1 beispielhaft, aber nicht einschränkend für CF3, R2 und R3 beispielhaft, aber nicht einschränkend für Fluor, R4 beispielhaft, aber nicht einschränkend für Chlor und X beispielhaft, aber nicht einschränkend für Schwefel. The synthesis of the key intermediate (Ha) described in Scheme 1 can also be applied to the preparation of similar intermediates, e.g. B. 3- (4-Chloro-2-fluoro-5-mercaptophenyl) -l-methyl -5,6-ditrifluoromethyl-1H-pyrimidine-2,4-dione (IIb). In this context, ethyl 4,4,4-trifluoro-3-oxo-2- (trifluoromethyl) butanoate (see Journal of Fluorine Chemistry (2016), 181, 1-6) is used as the starting material by way of example, but not by way of limitation. In scheme 1 below, R 1 is exemplary but not limiting for CF3, R 2 and R 3 are exemplary but not limiting for fluorine, R 4 is exemplary but not limiting for chlorine and X is exemplary but not limiting for sulfur.
Figure imgf000046_0001
Figure imgf000046_0001
Schema 2. Die betreffenden intermediären weiter substituierten N-Methyl-5-Mercaptophenyl-lH-pyrimidin-2,4- dione (II) können daraufhin auf verschiedenen Wegen in die gewünschten erfmdungsmeäßen Scheme 2. The intermediate further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-diones (II) in question can then be converted into the desired according to the invention in various ways
Verbindungen der allgemeinen Formel (Ia), bei denen X für Schwefel (S) und Y für Sauerstoff (O) stehen, überführt werden (Schema 3), nachdem die Verbindungen (II) in einem ersten Schritt mit Hilfe eines geeigneten, gegebenenfalls weiter substituierten Iod-Pyridons unter Verwendung einer geeigneten Base oder unter Verwendung eines geeigneten Übergangsmetallkatalysators (z. B. Compounds of the general formula (Ia) in which X is sulfur (S) and Y is oxygen (O) are transferred (scheme 3), after the compounds (II) in a first step with the aid of a suitable, optionally further substituted iodopyridone using a suitable base or using a suitable transition metal catalyst (e.g.
Tris(dibenzylidenaceton)dipalladium(0)) mit einem geeigneten Liganden (z. B. 4,5- Bis(diphenylphosphino)-9,9-dimethylxanthen) und einer geeigneten Base (z. B. Diispropyl(ethyl)amin) in einem geeigneten polar-aprotischen Lösemittel (z.B. Dioxan) zu Intermediaten (III) umgesetzt worden sind. Im nachfolgenden Schema 3 haben Q, R1, R2, R3 und R4 die obenstehenden Tris (dibenzylideneacetone) dipalladium (0)) with a suitable ligand (e.g. 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) and a suitable base (e.g. diispropyl (ethyl) amine) in one suitable polar aprotic solvents (eg dioxane) have been converted to intermediates (III). In Scheme 3 below, Q, R 1 , R 2 , R 3 and R 4 have the above
erfindungsgemäßen Bedeutungen. Weiterhin stehen R5, R6, R7 beispielhaft, aber nicht einschränkend für Wasserstoff, X beispielhaft, aber nicht einschränkend für Schwefel, Y beispielhaft, aber nicht einschränkend für Sauerstoff und G beispielhaft, aber nicht einschränkend für CH2. Das entsprechende beispielhaft, aber nicht einschränkend in Schema 2 beschriebene Intermediat (II) kann durch Umsetzung mit einem geeigneten, gegebenenfalls weiter substituierten Iodalkansäureester (in Schema 3 beispielhaft, aber nicht einschränkend ein Iodessigsäureester) unter Verwendung einer geeigneten Base (z.B. meanings according to the invention. Furthermore, R 5 , R 6 , R 7 are exemplary but not limiting for hydrogen, X are exemplary but not limiting for sulfur, Y are exemplary but not limiting for oxygen and G are exemplary but not limiting for CH 2 . The corresponding intermediate (II) described in Scheme 2 by way of example, but not by way of limitation, can be prepared by reaction with a suitable, optionally further substituted iodoalkanoic acid ester (in Scheme 3, for example, but not by way of limitation, an iodoacetic acid ester) using a suitable base (e.g.
Silber(I)carbonat) in einem geeigneten polar-aprotischen Lösemittel (z.B. n-Hexan oder Cyclohexan) bei erhöhter Temperatur (z.B. unter Mikrowellenbedingungen) in einen entsprechenden intermediären Oxyalkansäureester (IVa, IVb) oder die gewünschten Zielverbindungen der allgemeinen Formel (Ia) überführt werden (vgl. Synthesis 2009, 2725). Die entsprechenden Iodalkansäureester sind über literaturbekannte Wege herstellbar (vgl. Eur. J. Org. Chem., 2006, 71, 8459; WO2012037573; Silver (I) carbonate) in a suitable polar aprotic solvent (e.g. n-hexane or cyclohexane) at elevated temperature (e.g. under microwave conditions) into a corresponding intermediate oxyalkanoic acid ester (IVa, IVb) or the desired target compounds of the general formula (Ia) (see Synthesis 2009, 2725). The corresponding iodoalkanoic acid esters can be prepared by methods known from the literature (cf. Eur. J. Org. Chem., 2006, 71, 8459; WO2012037573;
Organometallics, 2009, 28, 132). Organometallics, 2009, 28, 132).
Figure imgf000047_0001
Schema 3
Figure imgf000047_0001
Scheme 3
Die intermediären Ethylester (IVa) und tert-Butylester (IVb) können danach unter geeigneten The intermediate ethyl esters (IVa) and tert-butyl esters (IVb) can then under suitable
Reaktionsbedingungen [Verwendung einer geeigneten Säure wie z. B. Salzsäure oder Essigsäure im Falle von (IVa) oder Trifluoressigsäure (TFA) im Falle von (IVb)] in die entsprechende freie Säure (V) überführt werden. Durch Reaktion der entsprechenden intermediären Säure (V) mit einer geeigneten Verbindung Q-H unter Vermittlung durch geeignete Kupplungsreagenzien (z. B. HOBt = 1- Hydroxybenzotriazol, EDC = l-Ethyl-3-(3-dimethylaminopropyl)carbodiimid, HATU = 0-(7- Azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium-hexafluorphosphat, T3P = 2,4,6-Tripropyl- l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxid) und geeignete Basen (z. B. Diisopropylethylamin, Triethylamin) in einem geeigneten polar-aprotischen Fösemittel (z. B. Dichlormethan, Chloroform) können die gewünschten substituierten N-Phenyluracile der allgemeinen Formel (Ia) hergestellt werden. Alternativ kann der Ethylester (IVa) durch Kupplung mit einer geeigneten Verbindung Q-H unter Vermittlung durch eine geeignete Fewissäure (z.B. Indium(III)chlorid) in das entsprechende gewünschte substituierte N-Phenyluracil der allgemeinen Formel (Ia) überführt werden (vgl. WO2011/1307088). Reaction conditions [using a suitable acid such as e.g. B. hydrochloric acid or acetic acid in the case of (IVa) or trifluoroacetic acid (TFA) in the case of (IVb)] can be converted into the corresponding free acid (V). By reaction of the corresponding intermediate acid (V) with a suitable compound QH with the mediation of suitable coupling reagents (e.g. HOBt = 1-hydroxybenzotriazole, EDC = 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, HATU = 0- ( 7-Azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, T3P = 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4 , 6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform), the desired substituted N-phenyluracils of the general formula (Ia) can be prepared. Alternatively, the ethyl ester (IVa) can be converted into the corresponding, desired substituted N-phenyluracil of the general formula (Ia) by coupling with a suitable compound QH with the mediation of a suitable Fewis acid (e.g. indium (III) chloride) (cf. WO2011 / 1307088 ).
Die Herstellung der Verbindungen der allgemeinen Formel (I), bei denen X und Y beispielhaft, aber nicht einschränkend für Sauerstoff (O) stehen, verläuft über die Synthese von Schlüsselintermediaten (VI) mit Fluorsubstituent an Position 5, wie z. B. 3-(2,5-Difluor-4-nitro)-l-methyl-6-trifluormethyl-lH- pyrimidin-2,4-dion (Via). Dazu wird ein geeignetes substituiertes Anilin, beispielhaft, aber nicht einschränkend, 2,5-Difluoranilin, mit einem geeigneten Reagenz (z. B. Triphosgen) in einem geeigneten polar-aprotischen Fösemittel (z. B. Dichlormethan) in das entsprechende Isocyanat überführt, das im nächsten Schritt durch Umsetzung mit einem geeigneten Aminoacrylsäureester unter Verwendung einer geeigneten Base (z. B. Natriumhydrid oder Kalium-tert-butylat) in einem geeigneten polar-aprotischen Fösemittel (z. B. N,N-Dimethylformamid) in das entsprechende gegebenenfalls weiter substituierte Pyrimidin-2,4-dion, hier beispielhaft, aber nicht einschränkend, 3-(2,5-Difluorphenyl)-6-trifluormethyl- lH-pyrimidin-2,4-dion, überführt wird (Schema 4). Durch Nitrierung mit einem geeigneten The preparation of the compounds of the general formula (I) in which X and Y are exemplary, but not restrictive, oxygen (O), proceeds via the synthesis of key intermediates (VI) with fluorine substituents at position 5, such as. B. 3- (2,5-Difluoro-4-nitro) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Via). For this purpose, a suitable substituted aniline, for example, but not limiting, 2,5-difluoroaniline, is converted into the corresponding isocyanate with a suitable reagent (e.g. triphosgene) in a suitable polar aprotic solvent (e.g. dichloromethane), this in the next step by reaction with a suitable amino acrylic acid ester using a suitable base (e.g. sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g. N, N-dimethylformamide) in the appropriate, if appropriate further substituted pyrimidine-2,4-dione, here by way of example but not limiting, 3- (2,5-difluorophenyl) -6-trifluoromethyl-1H-pyrimidine-2,4-dione, is converted (Scheme 4). By nitriding with a suitable
Nitrierungsreagenz und nachfolgende N-Methylierung mit einem geeigneten Methylierungsreagens erhält man das gewünschte Intermediat, hier beispielhaft, aber nicht einschränkend 3-(2,5-Difluor-4- nitro)-l-methyl-6-trifluormethyl-lH-pyrimidin-2,4-dion (Via). Im nachfolgenden Schema 4 stehen R1 beispielhaft, aber nicht einschränkend für Wasserstoff, R2 beispielhaft, aber nicht einschränkend für Fluor, R3 beispielhaft, aber nicht einschränkend für Fluor und R4 beispielhaft, aber nicht einschränkend für Nitro. Schema 4. Nitration reagent and subsequent N-methylation with a suitable methylation reagent gives the desired intermediate, here by way of example but not limitation 3- (2,5-difluoro-4-nitro) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2, 4-dione (via). In Scheme 4 below, R 1 is by way of example but not limiting for hydrogen, R 2 is by way of example but not limiting for fluorine, R 3 is by way of example but not limiting for fluorine and R 4 is by way of example but not limiting for nitro. Scheme 4.
Das auf die oben beschriebene Weise erhaltene Intermediat (VI), z. B. Verbindung (Via), kann danach mit einem geeigneten substituierten 2-Carbonylalkyloxy-3-hydroxypyridin (VII) unter Verwendung einer geeigneten Base (z. B. Kaliumcarbonat) in einem geeigneten polar-aprotischen Lösemittel (z. B. N,N-Dimethylformamid (DMF)) in ein gewünschtes substituiertes N-Phenyluracil (Ib, R4 = Nitro) überführt werden. Das dazu verwendete Intermediat (VII) kann durch mehrstufige Synthese ausgehend von kommerziell erhältlichem 2-Chlor-3-nitropyridin über (i) basenvermittelte Kupplung (z.B. mit Natriumhydrid) mit einem geeigneten substituierten Hydroxyalkylcarbonylreagenz in einem geeigneten polar-aprotischen Lösemittel (z. B. Tetrahydrofuran oder Dioxan), (ii) Reduktion der Nitrogruppe mit einem geeigneten Reduktionsmittel (z. B. Wasserstoff, Palladium auf Kohle in einem geeigneten polar- protischen Lösemittel), (iii) Diazotierung (mit einem geeigneten Diazotierungsreagenz, z.B. tert- Butylnitrit (t-BuONO), Bortrifluorid-Etherat (BF -OEt ) in geeigneten polar-aprotischen Lösemitteln (z.B. Dichlormethan (DCM), Dimethoxyethan), (iv) Umsetzung mit Acetanhydrid und (v) Freisetzung der Hydroxygruppe durch Abspaltung der Acetylschutzgruppe (z.B. basenvermittelt mit Kaliumcarbonat in einem polar-protischen Lösemittel) erhalten werden. Die Nitrogruppe in Verbindung (Ib) kann danach durch Reduktion und anschließende Sandmeyer-Reaktion in einen Halogensubstituenten (z.B. Chlor, Brom) überführt werden, so daß auf diese Weise das gewünschte substituierte N-Phenyluracil (Ic) erhalten werden kann. Im nachfolgenden Schema 5 haben Q, R1 und R2 die obenstehenden The intermediate (VI) obtained in the manner described above, e.g. B. Compound (Via), can then with a suitable substituted 2-carbonylalkyloxy-3-hydroxypyridine (VII) using a suitable base (e.g. potassium carbonate) in a suitable polar aprotic solvent (e.g. N, N -Dimethylformamide (DMF)) can be converted into a desired substituted N-phenyluracil (Ib, R 4 = nitro). The intermediate (VII) used for this can be synthesized in a multistage manner starting from commercially available 2-chloro-3-nitropyridine via (i) base-mediated coupling (e.g. with sodium hydride) with a suitable substituted hydroxyalkylcarbonyl reagent in a suitable polar-aprotic solvent (e.g. Tetrahydrofuran or dioxane), (ii) reduction of the nitro group with a suitable reducing agent (e.g. hydrogen, palladium on carbon in a suitable polar protic solvent), (iii) diazotization (with a suitable diazotization reagent, e.g. tert-butyl nitrite (t -BuONO), boron trifluoride etherate (BF -OEt) in suitable polar aprotic solvents (e.g. dichloromethane (DCM), dimethoxyethane), (iv) reaction with acetic anhydride and (v) release of the hydroxyl group by splitting off the acetyl protective group (e.g. base-mediated with potassium carbonate in a polar protic solvent) .The nitro group in compound (Ib) can then be obtained by reduction and subsequent S Andmeyer reaction can be converted into a halogen substituent (eg chlorine, bromine), so that the desired substituted N-phenyluracil (Ic) can be obtained in this way. In Scheme 5 below, Q, R 1 and R 2 are as above
erfindungsgemäßen Bedeutungen. Weiterhin stehen R3 beispielhaft, aber nicht einschränkend für Fluor, R4 beispielhaft, aber nicht einschränkend für Chlor oder Nitro, R5, R6, R7 beispielhaft, aber nicht einschränkend für Wasserstoff, X und Y beispielhaft, aber nicht einschränkend für Sauerstoff und G beispielhaft, aber nicht einschränkend für CH2. Schema 5. meanings according to the invention. Furthermore, R 3 is exemplary but not limiting for fluorine, R 4 is exemplary, but not limiting for chlorine or nitro, R 5 , R 6 , R 7 are exemplary but not limiting for hydrogen, X and Y are exemplary, but not limiting for oxygen and G are exemplary, but not limiting, of CH 2 . Scheme 5.
Das auf die oben beschriebene Weise erhaltene Intermediat (VI) kann entsprechend mit einem geeigneten substituierten 2-Carbonylalkylthio-3-hydroxypyridin (VIII) unter Verwendung einer geeigneten Base (z. B. Kaliumcarbonat) in einem geeigneten polar-aprotischen Lösemittel (z. B. N,N- Dimethylformamid (DMF)) in ein gewünschtes substituiertes N-Phenyluracil (Id, R4 = Nitro) mit X=0 (Sauerstoff) und Y=S (Schwefel) überführt werden. Das dazu verwendete Intermediat (VIII) kann durch mehrstufige Synthese analog zur in Schema 5 beschriebenen Synthese des Intermediates (VII) ausgehend von kommerziell erhältlichem 2-Chlor-3-nitropyridin hergestellt werden. Die Nitrogruppe in Verbindung (Id) kann danach durch Reduktion und anschließende Sandmeyer-Reaktion in einen Halogensubstituenten (z.B. Chlor, Brom) überführt werden, so daß auf diese Weise das gewünschte substituierte N-Phenyluracil (Ie) erhalten werden kann. Im nachfolgenden Schema 6 haben Q, R1 und R2 die obenstehenden erfmdungsgemäßen Bedeutungen. Weiterhin stehen R3 beispielhaft, aber nicht einschränkend für Fluor, R4 beispielhaft, aber nicht einschränkend für Chlor oder Nitro, R5, R6, R7 beispielhaft, aber nicht einschränkend für Wasserstoff, X steht beispielhaft, aber nicht einschränkend für Sauerstoff, Y steht beispielhaft, aber nicht einschränkend für Schwefel und G steht beispielhaft, aber nicht einschränkend für CH2. The intermediate (VI) obtained in the manner described above can correspondingly with a suitable substituted 2-carbonylalkylthio-3-hydroxypyridine (VIII) using a suitable base (e.g. potassium carbonate) in a suitable polar aprotic solvent (e.g. . N, N-dimethylformamide (DMF)) can be converted into a desired substituted N-phenyluracil (Id, R 4 = nitro) with X = 0 (oxygen) and Y = S (sulfur). The intermediate (VIII) used for this can be prepared by multistage synthesis analogous to the synthesis of the intermediate (VII) described in Scheme 5 starting from commercially available 2-chloro-3-nitropyridine. The nitro group in compound (Id) can then be converted into a halogen substituent (eg chlorine, bromine) by reduction and subsequent Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ie) can be obtained in this way. In scheme 6 below, Q, R 1 and R 2 have the meanings according to the invention above. Furthermore, R 3 is by way of example but not limiting for fluorine, R 4 is by way of example but not limiting for chlorine or nitro, R 5 , R 6 , R 7 are by way of example but not limiting for hydrogen, X is by way of example but not limiting for oxygen, Y stands for sulfur by way of example but not by way of limitation and G is by way of example but not by way of limitation for CH2.
Schema 6. Scheme 6.
Die intermediären weiter substituierten N-Methyl-5-Mercaptophenyl-lH-pyrimidin-2,4-dione (II) können auch in die gewünschten erfindungsgemäßen Verbindungen der allgemeinen Formel (If), bei denen X und Y für Schwefel (S) stehen, überführt werden (Schema 7), nachdem die Verbindungen (III) in einem ersten Schritt mit Hilfe eines geeigneten gegebenenfalls weiter substituierten Iod-Thiopyridins unter Verwendung einer geeigneten Base oder unter Verwendung eines geeigneten The intermediate, further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-diones (II) can also be converted into the desired compounds of the general formula (If) according to the invention, in which X and Y are sulfur (S), are converted (Scheme 7) after the compounds (III) in a first step with the aid of a suitable optionally further substituted iodo-thiopyridine with the use of a suitable base or with the use of a suitable one
Übergangsmetallkatalysators (z. B. Tris(dibenzylidenaceton)dipalladium(0)) mit einem geeigneten Liganden (z. B. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthen) und einer geeigneten Base (z. B. Diispropyl(ethyl)amin) in einem geeigneten polar-aprotischen Lösemittel (z.B. Dioxan) zu Transition metal catalyst (e.g. tris (dibenzylideneacetone) dipalladium (0)) with a suitable ligand (e.g. 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) and a suitable base (e.g. diispropyl ( ethyl amine) in a suitable polar-aprotic solvent (e.g. dioxane)
Intermediaten des Typs (IX) umgesetzt worden sind. Die Intermediate (IX) können dann mit unterschiedlich substituierten Halogenalkancarbonsäuren unter Verwendung von geeigneten Basen zu den gewünschten Verbindungen der allgemeinen Formel (If) umgesetzt werden. Im nachfolgenden Schema 6 haben Q, R1, R2, R3, und R4 die obenstehenden erfmdungsgemäßen Bedeutungen. Weiterhin stehen R5, R6, R7 beispielhaft, aber nicht einschränkend für Wasserstoff, X und Y beispielhaft, aber nicht einschränkend für Schwefel und G beispielhaft, aber nicht einschränkend für CH2. Weiterhin werden die Reaktionswege im folgenden Schema 7 zur besseren Klarheit beispielhaft, aber nicht einschränkend unter Verwendung von Iodessigsäureestem beschrieben. Es eignen sich auch vergleichbare Intermediates of type (IX) have been implemented. The intermediates (IX) can then be reacted with differently substituted haloalkanecarboxylic acids using suitable bases to give the desired compounds of the general formula (If). In scheme 6 below, Q, R 1 , R 2 , R 3 and R 4 have the meanings according to the invention above. Furthermore, R 5 , R 6 , R 7 are exemplary but not limiting for hydrogen, X and Y are exemplary but not limiting for sulfur and G are exemplary but not limiting for CH2. Furthermore, the reaction pathways are described in the following scheme 7 for better clarity by way of example, but not restrictively, using iodoacetic acid esters. Comparable ones are also suitable
Halogenalkancarbonsäuren (Halogen= Brom oder Chlor) zur Kupplung mit Intermediat (IX). Schema 7. Haloalkanecarboxylic acids (halogen = bromine or chlorine) for coupling with intermediate (IX). Scheme 7.
Ausgewählte detaillierte Synthesebeispiele für die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) sind im Folgenden aufgeführt. Die angegebenen Beispielnummem entsprechen den in den nachstehenden Tabellen F l bis F34 genannten Nummerierungen. Die ^-NMR-, 13C-NMR- und 19F- NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei 'H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei 19F-NMR, Lösungsmittel CDCF. CD3OD oder de-DMSO, interner Standard: Tetramethylsilan d = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, dq = Doppelquartett, dt = Doppeltriplett. Bei Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Hauptdiastereomers angegeben. Die verwendeten Abkürzungen für chemische Gruppen haben beispielsweise die nachfolgenden Bedeutungen: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t- Bu = C(CH3)3, n-Bu = unverzweigtes Butyl, n-Pr = unverzweigtes Propyl, i-Pr = verzweigtes Propyl, c- Pr = Cy clopropyl, c-Hex = Cyclohexyl. Synthesebeispiele: Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are listed below. The example numbers given correspond to the numbering given in Tables F 1 to F34 below. The ^ -NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 'H-NMR and 150 MHz for 13 C-NMR and 375 MHz at 19 F-NMR, CDCF solvent, CD3OD or de-DMSO, internal standard: tetramethylsilane d = 0.00 ppm), were obtained with an instrument from Bruker, and the signals indicated have the following meanings: br = broad ( it); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C (CH3) 2CH (CH3) 2, t-Bu = C (CH3) 3, n-Bu = unbranched butyl , n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-hex = cyclohexyl. Synthesis examples:
No. 1.1-1: 2-Methoxyethyl-{[3-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenyl}sulfanyl)pyridin-2-yl]oxy}acetat. No. 1.1-1: 2-Methoxyethyl - {[3 - ({2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H ) -yl] phenyl} sulfanyl) pyridin-2-yl] oxy} acetate.
Figure imgf000053_0001
Figure imgf000053_0001
2-Fluor-4-Chloranilin (145 g, 996 mmol) und Triethylamin (202 g, 2000 mmol) wurden nacheinander vorsichtig zu einer Lösung von Triphosgen (119 g, 401 mmol) in abs. Dichlormethan (1000 mL) gegeben, sodaß die Temperatur des resultierenden Reaktionsgemisches unter 20 °C blieb. Das 2-Fluoro-4-chloroaniline (145 g, 996 mmol) and triethylamine (202 g, 2000 mmol) were carefully added one after the other to a solution of triphosgene (119 g, 401 mmol) in abs. Dichloromethane (1000 mL) was added so that the temperature of the resulting reaction mixture remained below 20 ° C. The
Reaktionsgemisch wurde nach dem Ende der Zugabe über Nacht bei Raumtemperatur gerührt und danach mit Wasser (3 mal 500 mL) und IN Salzsäure (500 mL) gewaschen, über Natriumsulfat getrocknet, abfiltriert und bei vermindertem Druck eingeengt. Das so erhaltene 2-Fluor-4- Chlorphenylisocyanat wurde ohne weitere Reinigung im nächsten Schritt eingesetzt. Natriumhydrid (5.60 g, 140 mmol, 60%ige Dispersion in Mineralöl) wurde in abs. N,N-Dimethylformamid suspendiert und mit Ethyl-(2E)-3-amino-4,4,4-trifluorbut-2-enoat (14.2 g, 77.5 mmol) versetzt. Das After the addition was complete, the reaction mixture was stirred overnight at room temperature and then washed with water (3 times 500 ml) and 1N hydrochloric acid (500 ml), dried over sodium sulfate, filtered off and concentrated under reduced pressure. The 2-fluoro-4-chlorophenyl isocyanate thus obtained was used in the next step without further purification. Sodium hydride (5.60 g, 140 mmol, 60% dispersion in mineral oil) was in abs. Suspended N, N-dimethylformamide and mixed with ethyl (2E) -3-amino-4,4,4-trifluorobut-2-enoate (14.2 g, 77.5 mmol). The
Reaktionsgemisch wurde 1 h lang bei Raumtemperatur gerührt, danach auf eine Temperatur von -30 °C eingekühlt und mit 2-Fluor-4-Chlorphenylisocyanat (12.0 g, 70.0 mmol) versetzt. Das resultierende Reaktionsgemisch wurde nach vollständiger Zugabe 4 h lang bei Raumtemperatur nachgerührt und anschließend auf Eiswasser gegeben. Nach der Zugabe von Essigester und Ansäuern mit IN Salzsäure wurde die wäßrige Phase gründlich mit Essigester extrahiert. Die vereinigten organischen Phasen wurden mit Wasser gewaschen, über Natriumsulfat getrocknet, abfiltriert und unter vermindertem Druck eingeengt. Auf diese Weise wurde 3-(4-Chlor-2-fluorphenyl)-6-(trifluormethyl)pyrimidin-2,4(lH,3H)- dion (15.2 g, 50.2 mmol, 65%) erhalten, das ohne weitere Reinigung im nächsten Schritt eingesetzt wurde. Dieser Reaktionsschritt konnte auch im größeren Maßstab erfolgreich wiederholt werden. 3-(4- Chlor-2-fluorphenyl)-6-(trifluormethyl)pyrimidin-2,4(lH,3H)-dion (238 g, 770 mmol) wurde in abs. N,N-Dimethylformamid (800 mL) gelöst und mit Kaliumcarbonat (117 g, 850 mmol) versetzt. Danach wurde eine Lösung von Methyliodid (120 g, 850 mmol) in abs. N,N-Dimethylformamid (100 mL) zugegeben und das resultierende Reaktionsgemisch wurde 1 h lang bei Raumtemperatur nachgerührt. Nach vollständigem Umsatz wurde das Reaktionsgemsich auf eine Temperatur von 0°C eingekühlt, vorsichtig mit Wasser (2000 mL) versetzt und anschließend gründlich mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, abflitriert und unter vermindertem Druck eingeengt. Auf diese Weise wurde 3-(4-Chlor-2-fluorphenyl)-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion (241 g, 747 mmol, 97% der Theorie) erhalten, das im nächsten Schritt ohne weitere Reinigung umgesetzt wurde. 3-(4-Chlor-2-fluorphenyl)-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion (100 g, 310 mmol) wurde daraufhin schrittweise zu Chlorsulfonsäure in einem ausgeheizten Rundkolben gegeben. Das resultierende Reaktionsgemisch wurde danach 20 h lang bei einer Temperatur von 110 °C gerührt und nach dem Abkühlen auf Raumtemperatur auf Eiswasser gegeben und mehrfach mit Essigester extrahiert (3 mal 300 mL). Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, abfiltriert und unter vermindertem Druck eingeengt. Dadurch wurde 2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]benzensulfonylchlorid (75.0 g, 178 mmol, 57% der Theorie) erhalten, das ohne weitere Reinigung im nächsten Schritt eingesetzt wurde. 2-Chlor-4-fluor-5- [3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]sulfonylchlorid (100.0 g, 237 mmol) wurde in einem Rundkolben vorgelegt und nacheinander mit Salzsäure (500 mL), Essigsäure (500 mL) und Zinndichlorid-Dihydrat (270 g, 1197 mmol) versetzt. Das resultierende reaktionsgemisch wurde 10 h lang bei einer Temperatur von 100 °C gerührt, nach dem Abkühlen auf Raumtemperatur auf Eiswasser gegeben und gründlich mit Dichlormethan (3 mal 400 mL) extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, abfiltriert und unter vermindertem Druck eingeengt. Durch abschließende säulenchromatographische Reinigung wurde 3-(4-Chlor-2-fluor-5- sulfanylphenyl)-l-methyl-6-(trifluormethyl)pyrimidin-2,4(lH,3H)-dion (73.0 g, 206 mmol, 83% der Theorie) in Form eines farblosen Feststoffs erhalten. 3-(4-Chlor-2-fluor-5-sulfanylphenyl)-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion (1.69 mmol, 1 equiv.) wurde unter Argon in einem The reaction mixture was stirred at room temperature for 1 h, then cooled to a temperature of -30 ° C., and 2-fluoro-4-chlorophenyl isocyanate (12.0 g, 70.0 mmol) was added. After the addition was complete, the resulting reaction mixture was stirred for 4 hours at room temperature and then poured into ice water. After the addition of ethyl acetate and acidification with 1N hydrochloric acid, the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered off and concentrated under reduced pressure. In this way, 3- (4-chloro-2-fluorophenyl) -6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) - dione (15.2 g, 50.2 mmol, 65%) was obtained which, without further purification, was obtained in the next step was used. This reaction step could also be successfully repeated on a larger scale. 3- (4- chloro-2-fluorophenyl) -6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione (238 g, 770 mmol) was in abs. Dissolved N, N-dimethylformamide (800 mL) and combined with potassium carbonate (117 g, 850 mmol). Then a solution of methyl iodide (120 g, 850 mmol) in abs. N, N-dimethylformamide (100 mL) was added and the resulting reaction mixture was stirred at room temperature for 1 h. When the conversion was complete, the reaction mixture was cooled to a temperature of 0 ° C., water (2000 mL) was carefully added and the mixture was then extracted thoroughly with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. In this way, 3- (4-chloro-2-fluorophenyl) -l-methyl-6- (Trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione (241 g, 747 mmol, 97% of theory) was obtained, which was reacted in the next step without further purification. 3- (4-Chloro-2-fluorophenyl) -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione (100 g, 310 mmol) was then gradually added to chlorosulfonic acid in a heated round bottom flask . The resulting reaction mixture was then stirred for 20 h at a temperature of 110 ° C. and, after cooling to room temperature, poured into ice water and extracted several times with ethyl acetate (3 times 300 ml). The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. This gave 2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) -yl] benzenesulfonyl chloride (75.0 g, 178 mmol, 57% of theory), which was used in the next step without further purification. 2-Chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-l (2H) -yl] sulfonyl chloride (100.0 g, 237 mmol) was added in placed in a round bottom flask and successively mixed with hydrochloric acid (500 mL), acetic acid (500 mL) and tin dichloride dihydrate (270 g, 1197 mmol). The resulting reaction mixture was stirred for 10 hours at a temperature of 100 ° C., after cooling to room temperature it was poured onto ice water and extracted thoroughly with dichloromethane (3 times 400 ml). The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. Final purification by column chromatography gave 3- (4-chloro-2-fluoro-5-sulfanylphenyl) -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione (73.0 g, 206 mmol, 83 % of theory) in the form of a colorless solid. 3- (4-Chloro-2-fluoro-5-sulfanylphenyl) -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione (1.69 mmol, 1 equiv.) Was under argon in a
Mikrowellengefäß in Dioxan (16 mL) gelöst und nach dem Entgasen des Lösemittels mit Dissolved a microwave vessel in dioxane (16 mL) and, after degassing the solvent, with
Tris(dibenzylidenaceton)dipalladium (0.04 mmol), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthen (0.08 mmol), N,N-Diisopropylethylamin (3.37 mmol) und 3-Brom-2-hydroxypyridin 1.86 mmol) versetzt. Das resultierende Reaktionsgemisch wurde 2 h lang unter Mikrowellenbedingungen bei einer Temperatur von 160 °C gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch filtriert und das Filtrat eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Tris (dibenzylideneacetone) dipalladium (0.04 mmol), 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene (0.08 mmol), N, N-diisopropylethylamine (3.37 mmol) and 3-bromo-2-hydroxypyridine 1.86 mmol) were added . The resulting reaction mixture was stirred under microwave conditions at a temperature of 160 ° C for 2 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. Purification of the obtained by column chromatography
Rohproduktes wurde 3-{4-Chlor-2-fluor-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion (720 mg, 86 % der Theorie) in Form eines farblosen Feststoffs erhalten. 3-{4-Chlor-2-fhior-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion (300 mg, 0.67 mmol) wurde in einem Mikrowellengefäß unter Argon mit n-Hexan (17 mL) versetzt. Danach erfolgte die Zugabe von Silber(I)carbonat (223 mg, 0.80 mmol) und von Ethyl-2-iodacetat (0.16 ml, 1.34 mmol). Das Reaktionsgemisch wurde 30 Minuten lang bei einer Temperatur von 140 °C unter Mikrowellenbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch filtriert und das Filtrat unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes wurde Ethyl-{[3- ({2-chlor-4-fhior-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)- yl]phenyl}sulfanyl)pyridin-2-yl]oxy}acetat (84 mg, 34 % der Theorie) in Form eines farblosen Feststoffs erhalten. Ethyl-{[3-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenyl}sulfanyl)pyridin-2-yl]oxy}acetat (118 mg, 0.22 mmol) wurde in einem Rundkolben mit Essigsäure (2 mL) und konz. HCl (0.3 mL) versetzt. Das resultierende The crude product was 3- {4-chloro-2-fluoro-5 - [(2-hydroxypyridin-3-yl) sulfanyl] phenyl} -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (lH, 3H) - dione (720 mg, 86% of theory) obtained in the form of a colorless solid. 3- {4-chloro-2-fluor-5 - [(2-hydroxypyridin-3-yl) sulfanyl] phenyl} -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione ( 300 mg, 0.67 mmol) were mixed with n-hexane (17 mL) in a microwave vessel under argon. Then silver (I) carbonate (223 mg, 0.80 mmol) and ethyl 2-iodoacetate (0.16 ml, 1.34 mmol) were added. The reaction mixture was stirred for 30 minutes at a temperature of 140 ° C. under microwave conditions. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the crude product obtained by column chromatography gave ethyl - {[3- ({2-chloro-4-fluor-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 ( 2H) - yl] phenyl} sulfanyl) pyridin-2-yl] oxy} acetate (84 mg, 34% of theory) in the form of a colorless Solid obtained. Ethyl - {[3 - ({2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) -yl] phenyl} sulfanyl) pyridin-2-yl] oxy} acetate (118 mg, 0.22 mmol) was in a round bottom flask with acetic acid (2 mL) and conc. HCl (0.3 mL) were added. The resulting
Reaktionsgemisch wurde daraufhin 2h lang bei einer Temperatur von 50 °C gerührt und nach dem Abkühlen auf Raumtemperatur mit Wasser (5 mL) und Dichlormethan versetzt sowie extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, abfiltriert und unter The reaction mixture was then stirred for 2 hours at a temperature of 50 ° C. and, after cooling to room temperature, combined with water (5 mL) and dichloromethane and extracted. The combined organic phases were dried over sodium sulfate, filtered off and under
vermindertem Druck eingeengt. Durch abschließende präparative HPLC-Reinigung des erhaltenen Rohproduktes wurde{[3-({2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenyl}sulfanyl)pyridin-2-yl]oxy}essigsäure (60 mg, 51% der Theorie) in Form eines farblosen Feststoffs erhalten. {[3-({2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}sulfanyl)pyridin-2-yl]oxy}essigsäure (30 mg, 0.06 mmol) wurde in Dichlormethan gelöst und mit 1-Hydroxy-lH-benzotriazol -Hydrat (12 mg, 0.08 mmol), l-Ethyl-3-(3-dimethylaminopropyl)carbodiimid (15 mg, 0.08 mmol), 4-Dimethylaminopyridin (2 mg) sowie 2-Methoxyethanol (6 mg, 0.08 mmol) versetzt. Das resultierende Reaktionsgemisch wurde danach 2 h lang bei Raumtemperatur gerührt und eingeengt. Durch abschließende concentrated under reduced pressure. Final preparative HPLC purification of the crude product obtained gave {[3 - ({2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-l (2H) -yl] phenyl} sulfanyl) pyridin-2-yl] oxy} acetic acid (60 mg, 51% of theory) was obtained in the form of a colorless solid. {[3 - ({2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) -yl] phenyl} sulfanyl) pyridin-2-yl] oxy} acetic acid (30 mg, 0.06 mmol) was dissolved in dichloromethane and treated with 1-hydroxy-lH-benzotriazole hydrate (12 mg, 0.08 mmol), l-ethyl-3- (3-dimethylaminopropyl) carbodiimide (15 mg, 0.08 mmol), 4-dimethylaminopyridine (2 mg) and 2-methoxyethanol (6 mg, 0.08 mmol) are added. The resulting reaction mixture was then stirred at room temperature for 2 hours and concentrated. By final
säulenchromatographische Reinigung des erhaltenen Rohproduktes wurde 2-Methoxyethyl-{[3-({2- chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)- yl]phenyl}sulfanyl)pyridin-2-yl]oxy}acetat (22 mg, 64% der Theorie) in Form eines farblosen Feststoffs erhalten. ^-NMR (CDCE d, ppm) 8.08 (d, 1H), 7.65 (m, 1H), 7.35 (d, 1H), 7.25 (d, 1H), 6.92 (m, 1H), 6.29 (s, 1H), 5.00-4.89 (dd, 2H), 4.24-4.20 (m, 2H), 3.56 (m, 2H), 3.50 (s, 3H), 3.35 (s, 3H). Purification of the crude product obtained by column chromatography was 2-methoxyethyl - {[3 - ({2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H) - yl] phenyl} sulfanyl) pyridin-2-yl] oxy} acetate (22 mg, 64% of theory) was obtained in the form of a colorless solid. ^ -NMR (CDCE d, ppm) 8.08 (d, 1H), 7.65 (m, 1H), 7.35 (d, 1H), 7.25 (d, 1H), 6.92 (m, 1H), 6.29 (s, 1H) , 5.00-4.89 (dd, 2H), 4.24-4.20 (m, 2H), 3.56 (m, 2H), 3.50 (s, 3H), 3.35 (s, 3H).
No. 1.15-26: 3-Methoxypropyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl]phenoxy }pyridin-2-yl)oxy]acetat No. 1.15-26: 3-methoxypropyl - [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H) -yl] phenoxy} pyridin-2-yl) oxy] acetate
Figure imgf000055_0001
Figure imgf000055_0001
Ethyl- [(3 - {2-chlor-4-fluor-5 -[3 -methyl-2,6-dioxo-4-(trifluormethyl)-3 ,6-dihydropyrimidin- 1 (2H)- yl]phenoxy}pyridin-2-yl)oxy]acetat (2.00 g, 3.9 mmol) wurden in 50 ml Eisessig gelöst und 6 N wäßrige Salzsäure (5.34 ml, 32.1 mmol) wurden zugegeben. Der Ansatz wurde 6 h bei 50° C gerührt, über Nacht bei RT stehen gelassen, weitere 6 h bei 50° C gerührt, auf RT abgekühlt und mit Dichlormethan und Wasser versetzt. Die wäßrige Phase wurde abgetrennt. Die organische Phase wurde mit Wasser gewaschen, über Magnesiumsulfat getrocknet, und das Lösungsmittel wurde unter vermindertem Druck entfernt. Der Rückstand wurde säulenchromatographisch gereinigt (Gradient Essigsäureethylester/«-Heptan) und [(3-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]essigsäure (1.07 g, 2.10 mmol, 57 % der Theorie) wurde in Form eines hellbeigen Feststoffs erhalten. 'H-NMR (CDC1, d, ppm) 7.94-7.96 (m, 1H), 7.26- 7.39 (m, 2H), 6.96-6.99 (m, 1H), 6.78 (d, 1H), 6.32 (s, 1H), 4.91-5.00 (m, 2H), 3.51 (s, 3H). Zu einer Fösung aus 3-Methoxy-l-propanol (14 mg, 0.16 mmol) in 5 ml Dichlormethan wurde [(3-{2-Chlor-4- fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2F[)-yl]phenoxy}pyridin-2- yl)oxy]essigsäure (60 mg, 0.12 mmol) zugegeben und anschließend 1-Hydroxy-lH-benzotriazol Hydrat (24 mg, 0.16 mmol), l-(3-Dimethylaminopropyl)-3-ethylcarbodiimidhydrochlorid (31 mg, 0.16 mmol) und 4-Dimethylaminopyridin (10 mol%). Der Ansatz wurde 2 h bei RT gerührt, 4 d bei RT stehen gelassen, und weitere je 0.25 Äquivalente 1-Hydroxy-lH-benzotriazol Hydrat, l-(3- Dimethylaminopropyl)-3-ethylcarbodiimidhydrochlorid und 3-Methoxy-l-propanol wurden zugegeben. Der Ansatz wurde 6 h bei RT gerührt, über Nacht bei RT stehen gelassen und das Fösungsmittel wurde entfernt. Der Rückstand wurde säulenchromatographisch gereinigt (Gradient Essigsäureethylester/«- Heptan) und 3-Methoxypropyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetat (51 mg, Reinheit: 96 %, 71 % der Theorie) wurde in Form eines farblosen Feststoffs erhalten. 'H-NMR (CDC1 , d, ppm) 7.91-7.92 (m, 1H), 7.37 (d, 1H), 7.31-7.33 (m, 1H), 6.91-6.94 (m, 2H), 6.30 (s, 1H), 4.87-4.98 (m, 2H), 4.17-4.21 (m, 2H), 3.50- 3.51 (m, 3H), 3.37 (t, 2H), 3.29 (s, 3H), 1.83-1.91 (m, 2H). Ethyl [(3 - {2-chloro-4-fluoro-5 - [3 -methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) - yl] phenoxy} pyridine -2-yl) oxy] acetate (2.00 g, 3.9 mmol) was dissolved in 50 ml of glacial acetic acid and 6N aqueous hydrochloric acid (5.34 ml, 32.1 mmol) was added. The mixture was stirred at 50 ° C. for 6 h, left to stand at RT overnight, stirred at 50 ° C. for a further 6 h, cooled to RT and with Dichloromethane and water are added. The aqueous phase was separated off. The organic phase was washed with water, dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography (gradient ethyl acetate / «- heptane) and [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6- dihydropyrimidin-1 (2H) -yl] phenoxy} pyridin-2-yl) oxy] acetic acid (1.07 g, 2.10 mmol, 57% of theory) was obtained in the form of a light beige solid. 'H-NMR (CDC1, d, ppm) 7.94-7.96 (m, 1H), 7.26- 7.39 (m, 2H), 6.96-6.99 (m, 1H), 6.78 (d, 1H), 6.32 (s, 1H ), 4.91-5.00 (m, 2H), 3.51 (s, 3H). To a solution of 3-methoxy-1-propanol (14 mg, 0.16 mmol) in 5 ml of dichloromethane was added [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4 - (Trifluoromethyl) -3,6-dihydropyrimidin-1 (2F [) - yl] phenoxy} pyridin-2-yl) oxy] acetic acid (60 mg, 0.12 mmol) was added and then 1-hydroxy-1H-benzotriazole hydrate (24 mg, 0.16 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (31 mg, 0.16 mmol) and 4-dimethylaminopyridine (10 mol%). The batch was stirred for 2 h at RT, left to stand for 4 d at RT, and a further 0.25 equivalents each of 1-hydroxy-1H-benzotriazole hydrate, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 3-methoxy-1-propanol were added admitted. The mixture was stirred at RT for 6 h, left to stand at RT overnight and the solvent was removed. The residue was purified by column chromatography (gradient ethyl acetate / «- heptane) and 3-methoxypropyl - [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) - 3,6-dihydropyrimidin-1 (2H) -yl] phenoxy} pyridin-2-yl) oxy] acetate (51 mg, purity: 96%, 71% of theory) was obtained in the form of a colorless solid. 'H-NMR (CDC1, d, ppm) 7.91-7.92 (m, 1H), 7.37 (d, 1H), 7.31-7.33 (m, 1H), 6.91-6.94 (m, 2H), 6.30 (s, 1H ), 4.87-4.98 (m, 2H), 4.17-4.21 (m, 2H), 3.50-3.51 (m, 3H), 3.37 (t, 2H), 3.29 (s, 3H), 1.83-1.91 (m, 2H ).
No. 1.15-72: Tetrahydrofuran-3-ylmethyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)- 3 ,6-dihydropyrimidin- 1 (2H) -yl] phenoxy } pyridin-2-yl)oxy] acetat No. 1.15-72: Tetrahydrofuran-3-ylmethyl - [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3, 6-dihydropyrimidine-1 ( 2H) -yl] phenoxy} pyridin-2-yl) oxy] acetate
Figure imgf000056_0001
Figure imgf000056_0001
Zu einer Fösung aus Tetrahydro-3-furanmethanol (16 mg, 0.16 mmol) in 5 ml Dichlormethan wurde [(3- {2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)- yl]phenoxy}pyridin-2-yl)oxy]essigsäure (60 mg, 0.12 mmol) zugegeben und anschließend 1-Hydroxy- lH-benzotriazol Hydrat (24 mg, 0.16 mmol), l-(3-Dimethylaminopropyl)-3- ethylcarbodiimidhydrochlorid (31 mg, 0.16 mmol) und 4-Dimethylaminopyridin (10 mol%) zugesetzt. Der Ansatz wurde 2 h bei RT gerührt, über Nacht bei RT stehen gelassen, und weitere je 0.20 To a solution of tetrahydro-3-furanmethanol (16 mg, 0.16 mmol) in 5 ml of dichloromethane, [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- ( trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) - yl] phenoxy} pyridin-2-yl) oxy] acetic acid (60 mg, 0.12 mmol) was added, followed by 1-hydroxy-1H-benzotriazole hydrate (24 mg, 0.16 mmol), l- (3-dimethylaminopropyl) -3- ethylcarbodiimide hydrochloride (31 mg, 0.16 mmol) and 4-dimethylaminopyridine (10 mol%) were added. The batch was stirred at RT for 2 h, left to stand at RT overnight, and a further 0.20 each time
Äquivalente 1-Hydroxy-lH-benzotriazol Hydrat, l-(3-Dimethylaminopropyl)-3- ethylcarbodiimidhydrochlorid und 3-Methoxy-l-propanol wurden zugegeben. Der Ansatz wurde 6 h lang bei RT gerührt, über Nacht bei RT stehen gelassen und das Lösungsmittel wurde unter Equivalents of 1-hydroxy-1H-benzotriazole hydrate, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 3-methoxy-1-propanol were added. The mixture was stirred at RT for 6 h, left to stand at RT overnight and the solvent was removed
vermindertem Druck entfernt. Der Rückstand wurde säulenchromatographisch gereinigt (Gradient Essigsäureethylester/n-Heptan) und Tetrahydrofuran-3-ylmethyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6- dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetat (60 mg, Reinheit: 95 %, 81 % der Theorie) wurden erhalten. ' H-NIVIR (CDC1 , d, ppm) 7.90-7.91 (m, 1H), 7.38 (d, 1H), 7.29-7.31 (m, 1H), 6.89-6.94 (m, 2H), 6.30 (d, 1H), 4.87-4.99 (m, 2H), 3.97-4.16 (m, 2H), 3.68- 3.84 (m, 3H), 3.51 (s, 3H), 3.46-3.51 (m, 1H), 2.50-2.58 (m, 1H), 1.94-2.03 (m, 1H), 1.51-1.60 (m, 1H). removed under reduced pressure. The residue was purified by column chromatography (gradient ethyl acetate / n-heptane) and tetrahydrofuran-3-ylmethyl - [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl ) -3,6-dihydropyrimidin-1 (2H) -yl] phenoxy} pyridin-2-yl) oxy] acetate (60 mg, purity: 95%, 81% of theory) were obtained. 'H-NIVIR (CDC1, d, ppm) 7.90-7.91 (m, 1H), 7.38 (d, 1H), 7.29-7.31 (m, 1H), 6.89-6.94 (m, 2H), 6.30 (d, 1H ), 4.87-4.99 (m, 2H), 3.97-4.16 (m, 2H), 3.68-3.84 (m, 3H), 3.51 (s, 3H), 3.46-3.51 (m, 1H), 2.50-2.58 (m , 1H), 1.94-2.03 (m, 1H), 1.51-1.60 (m, 1H).
No. 1.15-350: [6-(Trifluormethyl)pyridin-3-yl]methyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetat No. 1.15-350: [6- (trifluoromethyl) pyridin-3-yl] methyl - [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) - 3,6-dihydropyrimidin-1 (2H) -yl] phenoxy} pyridin-2-yl) oxy] acetate
Figure imgf000057_0001
Figure imgf000057_0001
Zu einer Lösung aus [6-(Trifluormethyl)pyridin-3-yl]methanol (61 mg, 0.34 mmol) in 5 ml To a solution of [6- (trifluoromethyl) pyridin-3-yl] methanol (61 mg, 0.34 mmol) in 5 ml
Dichlormethan wurde [(3-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]essigsäure (120 mg, 0.25 mmol) zugegeben und anschließend mit 1-Hydroxy-lH-benzotriazol Hydrat (49 mg, 0.32 mmol), l-(3-Dimethylaminopropyl)- 3 -ethylcarbodiimidhydrochlorid (61 mg, 0.32 mmol) und 4-Dimethylaminopyridin (10 mol%) versetzt. Der Ansatz wurde 6 h bei RT gerührt, über Nacht bei RT stehen gelassen, und das Lösungsmittel wurde entfernt. Der Rückstand wurde über präparative HPLC gereinigt und [6-(Trifluormethyl)pyridin-3- yljmethyl- [(3 - {2-chlor-4-fluor-5 -[3 -methyl-2,6-dioxo-4-(trifluormethyl)-3 ,6-dihydropyrimidin- 1 (2H)- yl]phenoxy}pyridin-2-yl)oxy]acetat (95 mg, Reinheit: 98 %, 59 % der Theorie) wurden erhalten. Dichloromethane became [(3- {2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H) -yl] phenoxy} pyridine) -2-yl) oxy] acetic acid (120 mg, 0.25 mmol) was added and then 1-hydroxy-1H-benzotriazole hydrate (49 mg, 0.32 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (61 mg, 0.32 mmol) and 4-dimethylaminopyridine (10 mol%) are added. The mixture was stirred at RT for 6 h, left to stand at RT overnight, and the solvent was removed. The residue was purified by preparative HPLC and [6- (trifluoromethyl) pyridin-3-yljmethyl- [(3 - {2-chloro-4-fluoro-5 - [3 -methyl-2,6-dioxo-4- (trifluoromethyl ) -3, 6-dihydropyrimidin-1 (2H) - yl] phenoxy} pyridin-2-yl) oxy] acetate (95 mg, purity: 98%, 59% of theory) were obtained.
Tf-NMR (CDCL d, ppm) 8.65 (s, 1H), 7.80-7.84 (m, 2H), 7.66 (d, 1H), 7.37 (d, 1H), 7.27-7.30 (m, 1H), 6.91-6.94 (m, 1H), 6.85 (d, 1H), 6.29 (s, 1H), 5.26 (m, 2H), 4.93-5.04 (m, 2H), 3.51 (m, 3H). No. 1.31-23: 2-(2-Methoxyethoxy)ethyl-{[3-({5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl] -2-chlor-4-fluorphenyl } sulfanyl)-5 -fluorpyridin-2-yl] oxy } acetat Tf-NMR (CDCL d, ppm) 8.65 (s, 1H), 7.80-7.84 (m, 2H), 7.66 (d, 1H), 7.37 (d, 1H), 7.27-7.30 (m, 1H), 6.91- 6.94 (m, 1H), 6.85 (d, 1H), 6.29 (s, 1H), 5.26 (m, 2H), 4.93-5.04 (m, 2H), 3.51 (m, 3H). No. 1.31-23: 2- (2-methoxyethoxy) ethyl - {[3 - ({5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) -yl) ] -2-chloro-4-fluorophenyl} sulfanyl) -5-fluoropyridin-2-yl] oxy} acetate
Figure imgf000058_0001
Figure imgf000058_0001
3-(4-Chlor-2-fluor-5-sulfanylphenyl)-l-methyl-6-(trifluormethyl)pyrimidin-2,4(lH,3H)-dion (1.69 mmol, 1 equiv.) wurde unter Argon in einem Mikrowellengefaß in Dioxan (16 mL) gelöst und nach dem Entgasen des Lösemittels mit Tris(dibenzylidenaceton)dipalladium (0.04 mmol), 4,5- Bis(diphenylphosphino)-9,9-dimethylxanthen (0.08 mmol), N,N-Diisopropylethylamin (3.37 mmol) und 3-Brom-5-fluor-2-hydroxypyridin (1.86 mmol) versetzt. Das resultierende Reaktionsgemisch wurde 2 h lang unter Mikrowellenbedingungen bei einer Temperatur von 160 °C gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch filtriert und das Filtrat eingeengt. Durch 3- (4-Chloro-2-fluoro-5-sulfanylphenyl) -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione (1.69 mmol, 1 equiv.) Was under argon in a Microwave container dissolved in dioxane (16 mL) and after degassing the solvent with tris (dibenzylideneacetone) dipalladium (0.04 mmol), 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene (0.08 mmol), N, N-diisopropylethylamine ( 3.37 mmol) and 3-bromo-5-fluoro-2-hydroxypyridine (1.86 mmol) are added. The resulting reaction mixture was stirred under microwave conditions at a temperature of 160 ° C for 2 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. By
säulenchromatographische Reinigung des erhaltenen Rohproduktes wurde 3-{4-Chlor-2-fluor-5-[(5- fluor-2-hydroxypyridin-3 -yl)sulfanyl]phenyl } - 1 -methyl-6-(trifluormethyl)pyrimidin-2,4( lH,3H)-dion (600 mg, 76 % der Theorie) in Form eines farblosen Feststoffs erhalten. 3-{4-Chlor-2-fluor-5-[(5-fluor- 2-hydroxypyridin-3-yl)sulfanyl]phenyl}-l-methyl-6-(trifluormethyl)pyrimidin-2,4(lH,3H)-dion (300 mg, 0.64 mmol) wurde in einem Mikrowellengefäß unter Argon mit n-Hexan (17 mL) versetzt. Danach erfolgte die Zugabe von Silber(I)carbonat (213 mg, 0.77 mmol) und von 2-(2-Purification of the crude product obtained by column chromatography was 3- {4-chloro-2-fluoro-5 - [(5-fluoro-2-hydroxypyridin-3-yl) sulfanyl] phenyl} -1-methyl-6- (trifluoromethyl) pyrimidine-2 , 4 (1H, 3H) -dione (600 mg, 76% of theory) was obtained in the form of a colorless solid. 3- {4-Chloro-2-fluoro-5 - [(5-fluoro-2-hydroxypyridin-3-yl) sulfanyl] phenyl} -1-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H ) dione (300 mg, 0.64 mmol) was mixed with n-hexane (17 mL) in a microwave vessel under argon. This was followed by the addition of silver (I) carbonate (213 mg, 0.77 mmol) and of 2- (2-
Methoxyethoxy)ethyliodacetat (371 mg, 1.29 mmol). Das Reaktionsgemisch wurde 48 Minuten lang bei einer Temperatur von 140 °C unter Mikrowellenbedingungen gerührt. Nach dem Abkühlen auf Methoxyethoxy) ethyl iodoacetate (371 mg, 1.29 mmol). The reaction mixture was stirred for 48 minutes at a temperature of 140 ° C. under microwave conditions. After cooling down
Raumtemperatur wurde das Reaktionsgemisch filtriert und das Filtrat unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes wurde 2-(2- Methoxyethoxy)ethyl- { [3 -( { 5 -[3 -methyl-2,6-dioxo-4-(trifluormethyl)-3 ,6-dihydropyrimidin- 1 (2H)-yl] - 2-chlor-4-fluorphenyl}sulfanyl)-5-fluorpyridin-2-yl]oxy}acetat (72 mg, 18 % der Theorie) in Form eines farblosen Feststoffs erhalten. ' H-NMR (CDC1 , d, ppm) 7.85 (m, 1H), 7.43-7.39 (m, 2H), 7.24 (m, 1H), 6.33 (s, 1H), 4.95 (d, 1H), 4.91 (d, 1H), 4.29-4.25 (m, 2H), 3.72-3.66 (m, 2H), 3.64-3.61 (m, 2H), 3.58- 3.53 (m, 5H), 3.39 (s, 3H). The reaction mixture was filtered at room temperature and the filtrate was concentrated under reduced pressure. Purification of the crude product obtained by column chromatography gave 2- (2-methoxyethoxy) ethyl- {[3 - ({5 - [3 -methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H ) -yl] -2-chloro-4-fluorophenyl} sulfanyl) -5-fluoropyridin-2-yl] oxy} acetate (72 mg, 18% of theory) was obtained in the form of a colorless solid. 'H-NMR (CDC1, d, ppm) 7.85 (m, 1H), 7.43-7.39 (m, 2H), 7.24 (m, 1H), 6.33 (s, 1H), 4.95 (d, 1H), 4.91 ( d, 1H), 4.29-4.25 (m, 2H), 3.72-3.66 (m, 2H), 3.64-3.61 (m, 2H), 3.58-3.53 (m, 5H), 3.39 (s, 3H).
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten N- Heterocyclyl- und N-Heteroaryltetrahydropyrimidinonen erhält man die nachfolgend genannten Verbindungen. Wenn in Tabelle 1 ein Strukturelement durch eine Strukurformel definiert ist, welches eine gestrichelte Linie enthält, so bedeutet diese gestrichelte Linie, dass an dieser Position die betreffende Gruppe mit dem Rest des Moleküls verbunden ist. Wenn in Tabelle 1 ein Strukturelement durch eine Strukturformel definiert ist, welches einen Pfeil enthält, so steht der Pfeil für eine Bindung der jeweiligen Gruppe Q zur Carbonylgruppe in der allgemeinen Formel (I). In analogy to the preparation examples cited above and recited at the appropriate point and taking into account the general information on the preparation of substituted N-heterocyclyl- and N-heteroaryltetrahydropyrimidinones, the compounds mentioned below are obtained. If a structural element is defined by a structural formula in Table 1, which contains a dashed line, this dashed line means that the group in question is linked to the rest of the molecule at this position. If a structural element is defined in Table 1 by a structural formula which contains an arrow, the arrow stands for a bond between the respective group Q and the carbonyl group in the general formula (I).
Figure imgf000059_0001
Figure imgf000059_0001
Tabelle 1.1: Bevorzugte Verbindungen der Formel (1.1) sind die Verbindungen 1.1-1 bis 1.1-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.1-1 bis 1.1-440 der Tabelle 1.1 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q derTable 1.1: Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.1-1 to 1.1-440 of table 1.1 are thus due to the meaning of the respective entries No. 1 to 440 for Q der
Tabelle 1 definiert. Table 1 defined.
Tabelle 1: Table 1:
Figure imgf000059_0002
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0004
Figure imgf000071_0001
Figure imgf000059_0002
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0004
Figure imgf000071_0001
Tabelle 1.2: Bevorzugte Verbindungen der Formel (1.2) sind die Verbindungen 1.2-1 bis 1.2-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.2-1 bis 1.2-440 der Tabelle 1.2 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.2: Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.2-1 to 1.2-440 of Table 1.2 are thus identified by the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000071_0002
Tabelle 1.3: Bevorzugte Verbindungen der Formel (1.3) sind die Verbindungen 1.3-1 bis 1.3-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.3-1 bis 1.3-440 der Tabelle 1.3 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000071_0002
Table 1.3: Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.3-1 to 1.3-440 of Table 1.3 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000071_0003
Figure imgf000071_0003
Tabelle 1.4: Bevorzugte Verbindungen der Formel (F4) sind die Verbindungen F4-1 bis F4-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.4-1 bis F4-440 der Tabelle F4 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Tabelle 1.5: Bevorzugte Verbindungen der Formel (1.5) sind die Verbindungen 1.5-1 bis 1.5-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.5-1 bis 1.5-440 der Tabelle 1.5 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q derTable 1.4: Preferred compounds of the formula (F4) are the compounds F4-1 to F4-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.4-1 to F4-440 of table F4 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1. Table 1.5: Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.5-1 to 1.5-440 of Table 1.5 are thus due to the meaning of the respective entries No. 1 to 440 for Q der
Tabelle 1 definiert. Table 1 defined.
Figure imgf000072_0003
Tabelle 1.6: Bevorzugte Verbindungen der Formel (1.6) sind die Verbindungen 1.6-1 bis 1.6-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.6-1 bis 1.6-440 der Tabelle 1.6 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000072_0003
Table 1.6: Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.6-1 to 1.6-440 of Table 1.6 are thus identified by the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000072_0001
Figure imgf000072_0001
Tabelle 1.7: Bevorzugte Verbindungen der Formel (1.7) sind die Verbindungen 1.7-1 bis 1.7-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.7-1 bis 1.7-440 der Tabelle 1.7 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.7: Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.7-1 to 1.7-440 of Table 1.7 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000072_0002
Tabelle 1.8: Bevorzugte Verbindungen der Formel (1.8) sind die Verbindungen 1.8-1 bis 1.8-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.8-1 bis 1.8-440 der Tabelle 1.8 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000072_0002
Table 1.8: Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-440, in which Q has the meanings of Table 1 given in the respective line. The connections 1.8-1 to 1.8-440 of Table 1.8 are thus identified by the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000073_0001
Figure imgf000073_0001
Tabelle F9: Bevorzugte Verbindungen der Formel (F9) sind die Verbindungen F9-1 bis F9-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F9-1 bis F9-440 der Tabelle F9 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table F9: Preferred compounds of the formula (F9) are the compounds F9-1 to F9-440, in which Q has the meanings given in Table 1 in the respective line. The connections F9-1 to F9-440 of table F9 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000073_0002
Figure imgf000073_0002
Tabelle 1.10: Bevorzugte Verbindungen der Formel (F 10) sind die Verbindungen F 10-1 bis F 10-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F 10-1 bis F 10-440 der Tabelle F 10 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.10: Preferred compounds of the formula (F 10) are the compounds F 10-1 to F 10-440, in which Q has the meanings given in Table 1 in the respective line. The connections F 10-1 to F 10-440 of Table F 10 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000073_0003
Figure imgf000073_0003
Tabelle E l i : Bevorzugte Verbindungen der Formel (1.11) sind die Verbindungen 1.11-1 bis F l l-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F 11-1 bis F 11-440 der Tabelle F 11 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Tabelle 1.12: Bevorzugte Verbindungen der Formel (1.12) sind die Verbindungen 1.12-1 bis 1.12-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.12-1 bis 1.12-440 der Tabelle 1.12 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable E li: Preferred compounds of the formula (1.11) are the compounds 1.11-1 to F l-440, in which Q has the meanings of Table 1 given in the respective line. The connections F 11-1 to F 11-440 of Table F 11 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1. Table 1.12: Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.12-1 to 1.12-440 of Table 1.12 are thus due to the meaning of the respective entries No. 1 to
440 für Q der Tabelle 1 definiert. 440 defined for Q of Table 1.
Figure imgf000074_0002
Tabelle 1.13: Bevorzugte Verbindungen der Formel (F13) sind die Verbindungen F 13-1 bis F 13-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F 13-1 bis F 13-440 der Tabelle F13 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000074_0002
Table 1.13: Preferred compounds of the formula (F13) are the compounds F 13-1 to F 13-440, in which Q has the meanings given in Table 1 in the respective line. The connections F 13-1 to F 13-440 of table F13 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000074_0001
Figure imgf000074_0001
Tabelle E14: Bevorzugte Verbindungen der Formel (E14) sind die Verbindungen E 14-1 bis E 14-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E 14-1 bis E 14-440 der Tabelle E14 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table E14: Preferred compounds of the formula (E14) are the compounds E 14-1 to E 14-440, in which Q has the meanings given in Table 1 in the respective line. The connections E 14-1 to E 14-440 of table E14 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000074_0003
Tabelle E 15: Bevorzugte Verbindungen der Formel (E 15) sind die Verbindungen E 15-1 bis E 15-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E 15-1 bis E 15-440 der Tabelle E 15 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000074_0003
Table E 15: Preferred compounds of the formula (E 15) are the compounds E 15-1 to E 15-440, in which Q has the meanings given in Table 1 in the respective line. The connections E 15-1 to E 15-440 of Table E 15 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000075_0001
Figure imgf000075_0001
Tabelle 1.16: Bevorzugte Verbindungen der Formel (1.16) sind die Verbindungen 1.16-1 bis 1.16-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.16-1 bis 1.16-440 der Tabelle 1.16 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.16: Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.16-1 to 1.16-440 of table 1.16 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000075_0002
Figure imgf000075_0002
Tabelle 1.17: Bevorzugte Verbindungen der Formel (F 17) sind die Verbindungen F 17-1 bis F 17-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F 17-1 bis F 17-440 der Tabelle F 17 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.17: Preferred compounds of the formula (F 17) are the compounds F 17-1 to F 17-440, in which Q has the meanings given in Table 1 in the respective line. The connections F 17-1 to F 17-440 of table F 17 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000075_0003
Figure imgf000075_0003
Tabelle E l 8: Bevorzugte Verbindungen der Formel (E l 8) sind die Verbindungen E l 8-1 bis E l 8-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E 18-1 bis E 18-440 der Tabelle E 18 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Tabelle 1.19: Bevorzugte Verbindungen der Formel (1.19) sind die Verbindungen 1.19-1 bis 1.19-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.19-1 bis 1.19-440 der Tabelle 1.19 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable E l 8: Preferred compounds of the formula (E l 8) are the compounds E l 8-1 to E l 8-440, in which Q has the meanings given in Table 1 in the respective line. The connections E 18-1 to E 18-440 of Table E 18 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1. Table 1.19: Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.19-1 to 1.19-440 of Table 1.19 are thus due to the meaning of the respective entries No. 1 to
440 für Q der Tabelle 1 definiert. 440 defined for Q of Table 1.
Figure imgf000076_0001
Tabelle E20: Bevorzugte Verbindungen der Formel (E20) sind die Verbindungen E20-1 bis E20-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E20-1 bis E20-440 der Tabelle E20 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000076_0001
Table E20: Preferred compounds of the formula (E20) are the compounds E20-1 to E20-440, in which Q has the meanings given in Table 1 in the respective line. The connections E20-1 to E20-440 of table E20 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000076_0002
Figure imgf000076_0002
Tabelle 1.21: Bevorzugte Verbindungen der Formel (F21) sind die Verbindungen F21-1 bis F21-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F21-1 bis F21-440 der Tabelle F21 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.21: Preferred compounds of the formula (F21) are the compounds F21-1 to F21-440, in which Q has the meanings given in Table 1 in the respective line. The connections F21-1 to F21-440 of table F21 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000076_0003
Tabelle E22: Bevorzugte Verbindungen der Formel (E22) sind die Verbindungen E22-1 bis E22-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E22-1 bis E22-440 der Tabelle E22 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000076_0003
Table E22: Preferred compounds of the formula (E22) are the compounds E22-1 to E22-440, in which Q has the meanings given in Table 1 in the respective line. The connections E22-1 to E22-440 of table E22 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000077_0002
Figure imgf000077_0002
Tabelle 1.23: Bevorzugte Verbindungen der Formel (1.23) sind die Verbindungen 1.23-1 bis 1.23-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.23-1 bis 1.23-440 der Tabelle 1.23 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.23: Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.23-1 to 1.23-440 of table 1.23 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000077_0001
Figure imgf000077_0001
Tabelle E24: Bevorzugte Verbindungen der Formel (E24) sind die Verbindungen E24-1 bis E24-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E24-1 bis E24-440 der Tabelle E24 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table E24: Preferred compounds of the formula (E24) are the compounds E24-1 to E24-440, in which Q has the meanings given in Table 1 in the respective line. The connections E24-1 to E24-440 of table E24 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000077_0003
Figure imgf000077_0003
Tabelle 1.25: Bevorzugte Verbindungen der Formel (F25) sind die Verbindungen F25-1 bis F25-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F25-1 bis F25-440 der Tabelle F25 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Tabelle 1.26: Bevorzugte Verbindungen der Formel (1.26) sind die Verbindungen 1.26-1 bis 1.26-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.26-1 bis 1.26-440 der Tabelle 1.26 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.25: Preferred compounds of the formula (F25) are the compounds F25-1 to F25-440, in which Q has the meanings given in Table 1 in the respective line. The connections F25-1 to F25-440 in table F25 are therefore clear due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1. Table 1.26: Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.26-1 to 1.26-440 of Table 1.26 are thus due to the meaning of the respective entries No. 1 to
440 für Q der Tabelle 1 definiert. 440 defined for Q of Table 1.
Figure imgf000078_0001
Tabelle 1.27: Bevorzugte Verbindungen der Formel (F27) sind die Verbindungen F27-1 bis F27-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F27-1 bis F27-440 der Tabelle F27 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000078_0001
Table 1.27: Preferred compounds of the formula (F27) are the compounds F27-1 to F27-440, in which Q has the meanings given in Table 1 in the respective line. The connections F27-1 to F27-440 of table F27 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000078_0002
Figure imgf000078_0002
Tabelle E28: Bevorzugte Verbindungen der Formel (E28) sind die Verbindungen E28-1 bis E28-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E28-1 bis E28-440 der Tabelle E28 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table E28: Preferred compounds of the formula (E28) are the compounds E28-1 to E28-440, in which Q has the meanings given in Table 1 in the respective line. The connections E28-1 to E28-440 of table E28 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000078_0003
Tabelle 1.29: Bevorzugte Verbindungen der Formel (F29) sind die Verbindungen F29-1 bis F29-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F29-1 bis F29-440 der Tabelle F29 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000078_0003
Table 1.29: Preferred compounds of the formula (F29) are the compounds F29-1 to F29-440, in which Q has the meanings of Table 1 given in the respective line. The connections F29-1 to F29-440 of table F29 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000079_0003
Figure imgf000079_0003
Tabelle 1.30: Bevorzugte Verbindungen der Formel (1.30) sind die Verbindungen 1.30-1 bis 1.30-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.30-1 bis 1.30-440 der Tabelle 1.30 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table 1.30: Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.30-1 to 1.30-440 of Table 1.30 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
Figure imgf000079_0001
Figure imgf000079_0001
Tabelle E31 : Bevorzugte Verbindungen der Formel (E31) sind die Verbindungen E31-1 bis E31-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E31-1 bis E31-440 der Tabelle E31 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Table E31: Preferred compounds of the formula (E31) are the compounds E31-1 to E31-440, in which Q has the meanings given in Table 1 in the respective line. The connections E31-1 to E31-440 of table E31 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000079_0002
Figure imgf000079_0002
Tabelle E32: Bevorzugte Verbindungen der Formel (E32) sind die Verbindungen E32-1 bis E32-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E32-1 bis E32-440 der Tabelle E32 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. Tabelle 1.33: Bevorzugte Verbindungen der Formel (1.33) sind die Verbindungen 1.33-1 bis 1.33-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.33-1 bis 1.33-440 der Tabelle 1.33 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable E32: Preferred compounds of the formula (E32) are the compounds E32-1 to E32-440, in which Q has the meanings given in Table 1 in the respective line. The connections E32-1 to E32-440 of table E32 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1. Table 1.33: Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.33-1 to 1.33-440 of Table 1.33 are thus due to the meaning of the respective entries No. 1 to
440 für Q der Tabelle 1 definiert. 440 defined for Q of Table 1.
Figure imgf000080_0002
Tabelle 1.34: Bevorzugte Verbindungen der Formel (F34) sind die Verbindungen F34-1 bis F34-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen F34-1 bis F34-440 der Tabelle F34 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert.
Figure imgf000080_0002
Table 1.34: Preferred compounds of the formula (F34) are the compounds F34-1 to F34-440, in which Q has the meanings given in Table 1 in the respective line. The connections F34-1 to F34-440 in table F34 are thus due to the meaning of the respective entries no. 1 to 440 defined for Q of Table 1.
Figure imgf000080_0001
Figure imgf000080_0001
Tabelle E35: Bevorzugte Verbindungen der Formel (E35) sind die Verbindungen E35-1 bis E35-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen E35-1 bis E35-440 der Tabelle E35 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable E35: Preferred compounds of the formula (E35) are the compounds E35-1 to E35-440, in which Q has the meanings given in Table 1 in the respective line. The connections E35-1 to E35-440 of table E35 are thus due to the meaning of the respective entries No. 1 to
440 für Q der Tabelle 1 definiert. Tabelle 1.36: Bevorzugte Verbindungen der Formel (1.36) sind die Verbindungen 1.36-1 bis 1.36-440, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.36-1 bis 1.36-440 der Tabelle 1.36 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 440 für Q der Tabelle 1 definiert. 440 defined for Q of Table 1. Table 1.36: Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-440, in which Q has the meanings given in Table 1 in the respective line. The connections 1.36-1 to 1.36-440 of Table 1.36 are thus due to the meaning of the respective entries No. 1 to 440 defined for Q of Table 1.
NMR-Daten ausgewählter Beispiele: Die 'H-NMR-Daten ausgewählter Beispiele von Verbindungen der allgemeinen Formel (I) werden auf zwei verschiedene Weisen angegeben, und zwar (a) klassische NMR-Auswertung und Interpretation oder (b) in Form von 1H-NMR-Peaklisten nach der weiter unten beschriebenen Methode. a) klassische NMR-Interpretation NMR data of selected examples: The 'H-NMR data of selected examples of compounds of the general formula (I) are given in two different ways, namely (a) classical NMR evaluation and interpretation or (b) in the form of 1H- NMR peak lists according to the method described below. a) classical NMR interpretation
Beispiel Nr. 1.1-115 Example No. 1.1-115
'H-NMR (CDCfi d, ppm) 8.06 (d, 1H), 7.61 (m, 1H), 7.37 (d, 1H), 7.21 (m, 1H), 6.95-6.91 (m, 1H), 6.30 (s, 1H), 5.45-5.42 (m, 1H), 4.99-4.96 (d, 1H), 4.93-4.89 (d, 1H), 4.85 (m, 2H), 4.63 (m, 2H), 3.52 (s, 3H). 'H-NMR (CDCfi d, ppm) 8.06 (d, 1H), 7.61 (m, 1H), 7.37 (d, 1H), 7.21 (m, 1H), 6.95-6.91 (m, 1H), 6.30 (s , 1H), 5.45-5.42 (m, 1H), 4.99-4.96 (d, 1H), 4.93-4.89 (d, 1H), 4.85 (m, 2H), 4.63 (m, 2H), 3.52 (s, 3H ).
Beispiel Nr. 1.1-176 Example No. 1.1-176
'H-NMR (CDCfi d, ppm) 8.08 (d, 1H), 7.68 (m, 1H), 7.38 (d, 1H), 7.18 (d, 1H), 6.98-6.95 (m, 1H), 6.32 (s, 1H), 5.02-4.98 (d, 1H), 4.95-4.91 (d, 1H), 4.74 (s, 2H), 3.53 (s, 3H). 'H-NMR (CDCfi d, ppm) 8.08 (d, 1H), 7.68 (m, 1H), 7.38 (d, 1H), 7.18 (d, 1H), 6.98-6.95 (m, 1H), 6.32 (s , 1H), 5.02-4.98 (d, 1H), 4.95-4.91 (d, 1H), 4.74 (s, 2H), 3.53 (s, 3H).
Beispiel Nr. 1.1-286 Example No. 1.1-286
'H-NMR (CDCfi d, ppm) 8.57 (m, 1H), 8.06 (d, 1H), 7.70-7.63 (m, 2H), 7.34-7.28 (m, 2H), 7.26-7.21 (m, 2H), 6.94-6.91 (m, 1H), 6.23 (s, 1H), 5.29-5.26 (d, 1H), 5.24-5.20 (d, 1H), 5.07-5.03 (d, 1H), 5.01- 4.97 (d, 1H), 3.48 (s, 3H). 'H-NMR (CDCfi d, ppm) 8.57 (m, 1H), 8.06 (d, 1H), 7.70-7.63 (m, 2H), 7.34-7.28 (m, 2H), 7.26-7.21 (m, 2H) , 6.94-6.91 (m, 1H), 6.23 (s, 1H), 5.29-5.26 (d, 1H), 5.24-5.20 (d, 1H), 5.07-5.03 (d, 1H), 5.01-4.97 (d, 1H), 3.48 (s, 3H).
Beispiel Nr. 1.14-1 Example No. 1.14-1
'H-NMR (CDCfi d, ppm): 7.99 (dd, 1H), 7.87 (d, 1H), 7.51 (dd, 1H), 7.10 (d, 1H), 7.00 (dd, 1H), 6.28 (s, 1H), 4.94 (q, 1H), 4.21-4.18 (m, 2H), 3.52-3.50 (m, 5H), 3.30 (s, 3H). Beispiel Nr. 1.14-115 'H-NMR (CDCfi d, ppm): 7.99 (dd, 1H), 7.87 (d, 1H), 7.51 (dd, 1H), 7.10 (d, 1H), 7.00 (dd, 1H), 6.28 (s, 1H), 4.94 (q, 1H), 4.21-4.18 (m, 2H), 3.52-3.50 (m, 5H), 3.30 (s, 3H). Example No. 1.14-115
!H-NMR (CDCI3 d, ppm): 7.98 (dd, 1H), 7.88 (d, 1H), 7.50 (dd, 1H), 7.02-6.99 (m, 2H), 6.28 (s, 1H), 5.43-5.40 (quintet, 1H), 4.94 (q, 1H), 4.86-4.81 (m, 2H), 4.64-4.60 (m, 2H), 3.51 (s, 3H). ! H-NMR (CDCI 3 d, ppm): 7.98 (dd, 1H), 7.88 (d, 1H), 7.50 (dd, 1H), 7.02-6.99 (m, 2H), 6.28 (s, 1H), 5.43- 5.40 (quintet, 1H), 4.94 (q, 1H), 4.86-4.81 (m, 2H), 4.64-4.60 (m, 2H), 3.51 (s, 3H).
Beispiel Nr. 1.15-2 Example No. 1.15-2
!H-NMR (CDCI3 d, ppm) 7.92-7.90 (m, 1H), 7.37 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.91 (m, 2H), 6.29 (s, 1H), 5.02-4.91 (m, 2H), 4.26-4.23 (m, 2H), 3.60-3.57 (m, 2H), 3.51 (s, 3H), 3.47 (q, 2H), 1.17 (t, 3H). ! H-NMR (CDCl3 d, ppm) 7.92-7.90 (m, 1H), 7.37 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.91 (m, 2H), 6.29 (s, 1H), 5.02-4.91 (m, 2H), 4.26-4.23 (m, 2H), 3.60-3.57 (m, 2H), 3.51 (s, 3H), 3.47 (q, 2H), 1.17 (t, 3H).
Beispiel Nr. 1.15-71 Example No. 1.15-71
!H-NMR (CDCI3 d, ppm) 7.90-7.92 (m, 1H), 7.37 (d, 1H), 7.31-7.34 (m, 1H), 6.90-6.94 (m, 2H), 6.29 (m, 1H), 4.90-5.04 (m, 2H), 4.03-4.17 (m, 3H), 3.70-3.80 (m, 2H), 3.50 (m, 3H), 1.81-1.98 (m, 2H), 1.53-1.57 (m, 1H). ! H-NMR (CDCl3 d, ppm) 7.90-7.92 (m, 1H), 7.37 (d, 1H), 7.31-7.34 (m, 1H), 6.90-6.94 (m, 2H), 6.29 (m, 1H), 4.90-5.04 (m, 2H), 4.03-4.17 (m, 3H), 3.70-3.80 (m, 2H), 3.50 (m, 3H), 1.81-1.98 (m, 2H), 1.53-1.57 (m, 1H ).
Beispiel Nr. 1.15-211 Example No. 1.15-211
!H-NMR (CDCI3 d, ppm) 7.89-7.87 (m, 1H), 7.34 (d, 1H), 7.29 (d, 1H), 6.93-6.87 (m, 2H), 6.25 (s, 1H), 4.94-4.90 (d, 1H), 4.84-4.80 (d, 1H), 4.19-4.13 (m, 2H), 3.47 (s, 3H), 0.98-0.94 (m, 2H), -0.02 (s, 9H). ! H-NMR (CDCI 3 d, ppm) 7.89-7.87 (m, 1H), 7.34 (d, 1H), 7.29 (d, 1H), 6.93-6.87 (m, 2H), 6.25 (s, 1H), 4.94 -4.90 (d, 1H), 4.84-4.80 (d, 1H), 4.19-4.13 (m, 2H), 3.47 (s, 3H), 0.98-0.94 (m, 2H), -0.02 (s, 9H).
Beispiel Nr. 1.15-280 Example No. 1.15-280
^-NMR (CDCI3 d, ppm) 7.95 (m, 1H), 7.38-7.35 (m, 2H), 6.98-6.96 (m, 1H), 6.84-6.78 (d, 1H), 6.50 / 6.32 (s, 1H), 5.99 / 5.73 (s, 1H), 5.07-4.98 (m, 1H), 4.88-4.80 (m, 1H), 4.68-4.55 (m, 1H), 4.35-4.24 (m, 1H), 4.23 (br. m, 1H, NH), 4.12 (br. s, 1H, NH), 3.51 (s, 3H). ^ -NMR (CDCI3 d, ppm) 7.95 (m, 1H), 7.38-7.35 (m, 2H), 6.98-6.96 (m, 1H), 6.84-6.78 (d, 1H), 6.50 / 6.32 (s, 1H ), 5.99 / 5.73 (s, 1H), 5.07-4.98 (m, 1H), 4.88-4.80 (m, 1H), 4.68-4.55 (m, 1H), 4.35-4.24 (m, 1H), 4.23 (br . m, 1H, NH), 4.12 (br. s, 1H, NH), 3.51 (s, 3H).
Beispiel Nr. 1.15-288 Example No. 1.15-288
^-NMR (CDCI3 d, ppm) 8.57 (d, 1H), 7.88-7.90 (m, 1H), 7.36 (d, 1H), 7.30-7.32 (m, 1H), 7.17 (d, 1H), 6.94-6.96 (m, 1H), 6.84 (d, 1H), 6.25 (s, 1H), 5.17-5.21 (m, 2H), 5.03 (q, 2H), 3.49 (s, 3H). ^ -NMR (CDCI 3 d, ppm) 8.57 (d, 1H), 7.88-7.90 (m, 1H), 7.36 (d, 1H), 7.30-7.32 (m, 1H), 7.17 (d, 1H), 6.94 -6.96 (m, 1H), 6.84 (d, 1H), 6.25 (s, 1H), 5.17-5.21 (m, 2H), 5.03 (q, 2H), 3.49 (s, 3H).
Beispiel Nr. 1.15-350 Example No. 1.15-350
!H-NMR (CDCI3 d, ppm) 8.65 (d, 1H), 7.85-7.80 (m, 2H), 7.67 (d, 1H), 7.38 (d, 1H), 7.30-7.28 (m, 1H), 6.94-6.92 (m, 1H), 6.86 (d, 1H), 6.29 (s, 1H), 5.26 (s, 2H), 5.04-4.93 (q, 2H), 3.51 (s, 3H). ! H-NMR (CDCI 3 d, ppm) 8.65 (d, 1H), 7.85-7.80 (m, 2H), 7.67 (d, 1H), 7.38 (d, 1H), 7.30-7.28 (m, 1H), 6.94 -6.92 (m, 1H), 6.86 (d, 1H), 6.29 (s, 1H), 5.26 (s, 2H), 5.04-4.93 (q, 2H), 3.51 (s, 3H).
Beispiel Nr. 1.15-366 Example No. 1.15-366
^-NMR (CDCI3 d, ppm) 7.87-7.85 (m, 1H), 7.37 (d, 1H), 7.29 (s, 1H), 7.28-7.26 (m, 1H), 6.92-6.87 (m, 2H), 6.30 (s, 1H), 4.99 (s, 2H), 4.90 (dd, 2H), 3.79 (s, 3H), 3.52 (s, 3H), 2.18 (s, 3H). Beispiel Nr. 1.15-367 ^ -NMR (CDCI 3 d, ppm) 7.87-7.85 (m, 1H), 7.37 (d, 1H), 7.29 (s, 1H), 7.28-7.26 (m, 1H), 6.92-6.87 (m, 2H) , 6.30 (s, 1H), 4.99 (s, 2H), 4.90 (dd, 2H), 3.79 (s, 3H), 3.52 (s, 3H), 2.18 (s, 3H). Example No. 1.15-367
'H-NMR (CDCI3 d, ppm) 7.88-7.86 (m, 1H), 7.38-7.35 (m, 2H), 7.28-7.26 (m, 1H), 6.92-6.88 (m, 2H), 6.30 (s, 1H), 4.99 (s, 2H), 4.90 (dd, 2H), 3.76 (s, 3H), 3.52 (s, 3H), 2.21 (s, 3H). 'H-NMR (CDCI 3 d, ppm) 7.88-7.86 (m, 1H), 7.38-7.35 (m, 2H), 7.28-7.26 (m, 1H), 6.92-6.88 (m, 2H), 6.30 (s , 1H), 4.99 (s, 2H), 4.90 (dd, 2H), 3.76 (s, 3H), 3.52 (s, 3H), 2.21 (s, 3H).
Beispiel Nr. 1.15-368 Example No. 1.15-368
'H-NMR (CDCI3 d, ppm) 7.86-7.85 (m, 1H), 7.36 (d, 1H), 7.33 (s, 1H), 7.28-7.26 (m, 1H), 6.92-6.88 (m, 2H), 6.30 (s, 1H), 5.00 (s, 2H), 4.91 (dd, 2H), 4.06 (q, 2H), 3.52 (s, 3H), 2.20 (s, 3H), 1.45 (t, 3H). 'H-NMR (CDCI 3 d, ppm) 7.86-7.85 (m, 1H), 7.36 (d, 1H), 7.33 (s, 1H), 7.28-7.26 (m, 1H), 6.92-6.88 (m, 2H ), 6.30 (s, 1H), 5.00 (s, 2H), 4.91 (dd, 2H), 4.06 (q, 2H), 3.52 (s, 3H), 2.20 (s, 3H), 1.45 (t, 3H) .
Beispiel Nr. 1.15-421 Example No. 1.15-421
'H-NMR (CDCI3 d, ppm) 7.93-7.91 (m, 1H), 7.38-7.33 (m, 2H), 6.95-6.92 (m, 1H), 6.90-6.87 (m, 1H), 6.29 (s, 1H), 5.02 (d, 1H), 4.96 (d, 1H), 4.46-4.44 (m, 1H), 4.12-4.08 (m, 2H), 3.50 (s, 3H), 3.33 (s, 3H), 3.32 (s, 3H). 'H-NMR (CDCl3 d, ppm) 7.93-7.91 (m, 1H), 7.38-7.33 (m, 2H), 6.95-6.92 (m, 1H), 6.90-6.87 (m, 1H), 6.29 (s, 1H), 5.02 (d, 1H), 4.96 (d, 1H), 4.46-4.44 (m, 1H), 4.12-4.08 (m, 2H), 3.50 (s, 3H), 3.33 (s, 3H), 3.32 (s, 3H).
Beispiel Nr. 1.15-422 Example No. 1.15-422
'H-NMR (CDCI3 d, ppm) 7.92-7.90 (m, 1H), 7.38-7.31 (m, 2H), 6.95-6.88 (m, 2H), 6.29 (s, 1H), 5.02 (d, 1H), 4.96 (d, 1H), 4.63-4.60 (m, 1H), 4.12-4.07 (m, 2H), 3.69-3.61 (m, 2H), 3.55-3.48 (m, 5H), 1.19 (t, 3H). 'H-NMR (CDCI 3 d, ppm) 7.92-7.90 (m, 1H), 7.38-7.31 (m, 2H), 6.95-6.88 (m, 2H), 6.29 (s, 1H), 5.02 (d, 1H ), 4.96 (d, 1H), 4.63-4.60 (m, 1H), 4.12-4.07 (m, 2H), 3.69-3.61 (m, 2H), 3.55-3.48 (m, 5H), 1.19 (t, 3H ).
Beispiel Nr. 1.16-1 Example No. 1.16-1
'H-NMR (CDCI3 d, ppm) 7.92-7.90 (m, 1H), 7.53 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.92 (m, 1H), 6.88 (d, 1H), 6.28 (s, 1H), 5.01 (d, 1H), 4.94 (d, 1H), 4.27-4.20 (m, 2H), 3.55-3.51 (m, 2H), 3.50 (s, 3H), 3.31 (s, 3H). 'H-NMR (CDCl3 d, ppm) 7.92-7.90 (m, 1H), 7.53 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.92 (m, 1H), 6.88 (d, 1H) , 6.28 (s, 1H), 5.01 (d, 1H), 4.94 (d, 1H), 4.27-4.20 (m, 2H), 3.55-3.51 (m, 2H), 3.50 (s, 3H), 3.31 (s , 3H).
Beispiel Nr. 1.16-2 Example No. 1.16-2
'H-NMR (CDCI3 d, ppm) 7.92-7.90 (m, 1H), 7.54 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.87 (m, 2H), 6.29 (s, 1H), 5.02 (d, 1H), 4.95 (d, 1H), 4.26-4.23 (m, 2H), 3.60-3.58 (m, 2H), 3.50 (s, 3H), 3.47 (q, 2H), 1.17 (t, 3H). 'H-NMR (CDCI 3 d, ppm) 7.92-7.90 (m, 1H), 7.54 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.87 (m, 2H), 6.29 (s, 1H ), 5.02 (d, 1H), 4.95 (d, 1H), 4.26-4.23 (m, 2H), 3.60-3.58 (m, 2H), 3.50 (s, 3H), 3.47 (q, 2H), 1.17 ( t, 3H).
Beispiel Nr. 1.16-23 Example No. 1.16-23
'H-NMR (CDCI3 d, ppm) 7.92-7.90 (m, 1H), 7.54 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.87 (m, 2H), 6.29 (s, 1H), 5.02 (d, 1H), 4.94 (d, 1H), 4.27-4.25 (m, 2H), 3.69-3.66 (m, 2H), 3.62-3.59 (m, 2H), 3.53-3.51 (m, 2H), 3.50 (s, 3H), 3.37 (s, 3H). 'H-NMR (CDCl3 d, ppm) 7.92-7.90 (m, 1H), 7.54 (d, 1H), 7.34-7.31 (m, 1H), 6.94-6.87 (m, 2H), 6.29 (s, 1H) , 5.02 (d, 1H), 4.94 (d, 1H), 4.27-4.25 (m, 2H), 3.69-3.66 (m, 2H), 3.62-3.59 (m, 2H), 3.53-3.51 (m, 2H) , 3.50 (s, 3H), 3.37 (s, 3H).
Beispiel Nr. 1.16-41 Example No. 1.16-41
'H-NMR (CDCB d, ppm): 7.91 (dd, 1H), 7.54 (d, 1H), 7.32 (dd, 1H), 6.93 (dd, 1H), 6.79 (d, 1H), 6.31 (s, 1H), 4.96 (q, 2H), 4.38-4.20 (m, 2H), 4.11 (t, 2H), 3.50 (s, 3H). Beispiel Nr. 1.16-71 'H-NMR (CDCB d, ppm): 7.91 (dd, 1H), 7.54 (d, 1H), 7.32 (dd, 1H), 6.93 (dd, 1H), 6.79 (d, 1H), 6.31 (s, 1H), 4.96 (q, 2H), 4.38-4.20 (m, 2H), 4.11 (t, 2H), 3.50 (s, 3H). Example No. 1.16-71
!H-NMR (CDCI3 d, ppm): 7.92 (dd, 1H), 7.53 (d, 1H), 7.33 (dd, 1H), 6.94-6.87 (m, 2H), 6.28 (s, 1H), 4.97 (pseudo quintet, 2H), 4.20-4.12 (m, 1H), 4.10-4.00 (m, 2H), 3.81-3.68 (m, 2H), 3.50 (s, 3H), 1.98- 1180 (m, 3H), 1.60-1.50 (m, 1H). ! H-NMR (CDCI 3 d, ppm): 7.92 (dd, 1H), 7.53 (d, 1H), 7.33 (dd, 1H), 6.94-6.87 (m, 2H), 6.28 (s, 1H), 4.97 ( pseudo quintet, 2H), 4.20-4.12 (m, 1H), 4.10-4.00 (m, 2H), 3.81-3.68 (m, 2H), 3.50 (s, 3H), 1.98-1180 (m, 3H), 1.60 -1.50 (m, 1H).
Beispiel Nr. 1.16-115 Example No. 1.16-115
^-NMR (CDCI3 d, ppm): 7.91 (dd, 1H), 7.53 (d, 1H), 7.32 (dd, 1H), 6.94 (dd, 1H), 6.82 (d, 1H), 6.29 (s, 1H), 5.49-5.43 (quintet, 1H), 4.96 (q, 1H), 4.84 (m, 2H), 4.62 (m, 2H), 3.51 (s, 3H). ^ -NMR (CDCI3 d, ppm): 7.91 (dd, 1H), 7.53 (d, 1H), 7.32 (dd, 1H), 6.94 (dd, 1H), 6.82 (d, 1H), 6.29 (s, 1H ), 5.49-5.43 (quintet, 1H), 4.96 (q, 1H), 4.84 (m, 2H), 4.62 (m, 2H), 3.51 (s, 3H).
Beispiel Nr. 1.16-176 Example No. 1.16-176
*H-NMR (CDCI3 d, ppm) 7.94-7.92 (m, 1H), 7.56 (d, 1H), 7.38-7.35 (m, 1H), 6.99-6.95 (m, 1H), 6.77- 6.74 (m, 1H), 6.31 (s, 1H), 5.04-5.00 (d, 1H), 4.97-4.93 (d, 1H), 4.74 (s, 2H), 3.51 (s, 3H). * H-NMR (CDCl3 d, ppm) 7.94-7.92 (m, 1H), 7.56 (d, 1H), 7.38-7.35 (m, 1H), 6.99-6.95 (m, 1H), 6.77- 6.74 (m, 1H), 6.31 (s, 1H), 5.04-5.00 (d, 1H), 4.97-4.93 (d, 1H), 4.74 (s, 2H), 3.51 (s, 3H).
Beispiel Nr. 1.16-286 Example No. 1.16-286
!H-NMR (CDCI3 d, ppm): 8.53 (d, 1H), 7.90 (dd, 1H), 7.67 (dt, 1H), 7.52 (d, 1H), 7.34 (dd, 1H), 7.29- 7.28 (d, 1H), 7.22 (dd, 1H), 6.92 (dd, 1H), 6.85 (d, 1H), 6.23 (s, 1H), 5.26 (pseudo t, 2H), 5.09-4.99 (q, 2H), 3.48 (s, 3H). ! H-NMR (CDCI 3 d, ppm): 8.53 (d, 1H), 7.90 (dd, 1H), 7.67 (dt, 1H), 7.52 (d, 1H), 7.34 (dd, 1H), 7.29- 7.28 ( d, 1H), 7.22 (dd, 1H), 6.92 (dd, 1H), 6.85 (d, 1H), 6.23 (s, 1H), 5.26 (pseudo t, 2H), 5.09-4.99 (q, 2H), 3.48 (s, 3H).
Beispiel Nr. 1.16-301 Example No. 1.16-301
'H-NMR (CDCI3 d, ppm): 9.14 (dd, 1H), 7.89 (dd, 1H), 7.54-7.45 (m, 3H), 7.33 (dd, 1H), 6.939 (dd, 1H), 6.78 (d, 1H), 6.26 (s, 1H), 5.50 (q, 2H), 5.04 (q, 2H), 3.50 (s, 3H). 'H-NMR (CDCl3 d, ppm): 9.14 (dd, 1H), 7.89 (dd, 1H), 7.54-7.45 (m, 3H), 7.33 (dd, 1H), 6.939 (dd, 1H), 6.78 ( d, 1H), 6.26 (s, 1H), 5.50 (q, 2H), 5.04 (q, 2H), 3.50 (s, 3H).
Beispiel Nr. 1.16-421 Example No. 1.16-421
^-NMR (CDCI3 d, ppm) 7.93-7.91 (m, 1H), 7.54 (d, 1H), 7.35-7.33 (m, 2H), 6.95-6.92 (m, 1H), 6.86 (d, 1H), 6.29 (s, 1H), 5.00 (d, 1H), 4.95 (d, 1H), 4.46-4.44 (m, 1H), 4.12-4.06 (m, 2H), 3.50 (s, 3H), 3.33 (s, 3H), 3.32 (s, 3H). ^ -NMR (CDCI3 d, ppm) 7.93-7.91 (m, 1H), 7.54 (d, 1H), 7.35-7.33 (m, 2H), 6.95-6.92 (m, 1H), 6.86 (d, 1H), 6.29 (s, 1H), 5.00 (d, 1H), 4.95 (d, 1H), 4.46-4.44 (m, 1H), 4.12-4.06 (m, 2H), 3.50 (s, 3H), 3.33 (s, 3H), 3.32 (s, 3H).
Beispiel Nr. 1.16-424 Example No. 1.16-424
!H-NMR CDCl d, ppm): 7.92 (dd, 1H), 7.53 (d, 1H), 7.34 (dd, 1H), 6.93 (dd, 1H), 6.87 (d, 1H), 6.29 (s, 1H), 5.07 (t, 1H), 4.99 (q, 2H), 4.15 (pseudo q, 2H), 3.96-3.86 (m, 4H), 3.50 (s, 3H). ! H-NMR CDCl d, ppm): 7.92 (dd, 1H), 7.53 (d, 1H), 7.34 (dd, 1H), 6.93 (dd, 1H), 6.87 (d, 1H), 6.29 (s, 1H) , 5.07 (t, 1H), 4.99 (q, 2H), 4.15 (pseudo q, 2H), 3.96-3.86 (m, 4H), 3.50 (s, 3H).
Beispiel Nr. 1.31-1 Example No. 1.31-1
^-NMR (CDCI3 d, ppm) 7.85 (m, 1H), 7.42-7.38 (m, 2H), 7.27 (m, 1H), 6.32 (s, 1H), 4.95 (d, 1H), 4.91 (d, 1H), 4.28-4.23 (m, 2H), 3.59-3.55 (m, 2H), 3.53 (s, 3H), 3.36 (s, 3H). Beispiel Nr. 1.35-23 ^ -NMR (CDCI 3 d, ppm) 7.85 (m, 1H), 7.42-7.38 (m, 2H), 7.27 (m, 1H), 6.32 (s, 1H), 4.95 (d, 1H), 4.91 (d , 1H), 4.28-4.23 (m, 2H), 3.59-3.55 (m, 2H), 3.53 (s, 3H), 3.36 (s, 3H). Example No. 1.35-23
!H-NMR (CDCI3 d, ppm): 8.00 (dd, 1H), 7.54-7.49 (m, 2H), 7.00 (dd, 1H), 6.97 (d, 1H), 6.28 (s, 1H), 4.93 (q, 1H), 4.23-4.20 (m, 2H), 3.67-3.65 (m, 2H), 3.61-3.59 (m, 2H), 3.54-3.49 (m, 5H), 3.37 (s, 3H). ! H-NMR (CDCI 3 d, ppm): 8.00 (dd, 1H), 7.54-7.49 (m, 2H), 7.00 (dd, 1H), 6.97 (d, 1H), 6.28 (s, 1H), 4.93 ( q, 1H), 4.23-4.20 (m, 2H), 3.67-3.65 (m, 2H), 3.61-3.59 (m, 2H), 3.54-3.49 (m, 5H), 3.37 (s, 3H).
Beispiel Nr. F35-41 Example no.F35-41
!ff-NMR (DMSO-De d, ppm): 8.19 (d, 1H), 8.06 (dd, 1H), 7.80 (dd, 1H), 7.17 (dd, 1H), 7.06 (d, 1H), 6.56 (s, 1H), 4.94 (ps q, 2H), 4.33-4.29 (m, 2H), 4.26-4.22 (m, 2H), 3.36 (s, 3H). ! ff-NMR (DMSO-De d, ppm): 8.19 (d, 1H), 8.06 (dd, 1H), 7.80 (dd, 1H), 7.17 (dd, 1H), 7.06 (d, 1H), 6.56 (s , 1H), 4.94 (ps q, 2H), 4.33-4.29 (m, 2H), 4.26-4.22 (m, 2H), 3.36 (s, 3H).
Beispiel Nr. 1.35-176 Example No. 1.35-176
!H-NMR (CDCI3 d, ppm): 8.02 (dd, 1H), 7.57-7.52 (m, 2H), 7.05 (dd, 1H), 6.80 (d, 1H), 6.28 (s, 1H), 4.96 (q, 2H), 4.72 (s, 2H), 3.51 (s, 3H). ! H-NMR (CDCI 3 d, ppm): 8.02 (dd, 1H), 7.57-7.52 (m, 2H), 7.05 (dd, 1H), 6.80 (d, 1H), 6.28 (s, 1H), 4.96 ( q, 2H), 4.72 (s, 2H), 3.51 (s, 3H).
Beispiel Nr. 1.35-286 Example No. 1.35-286
!H-NMR (CDCI3 d, ppm): 8.53 (d, 1H), 7.96 (dd, 1H), 7.72 (dt, 1H), 7.53 (dd, 1H), 7.49 (d, 1H), 7.30- 7.22 (m, 2H), 6.99 (dd, 1H), 6.93 (d, 1H), 6.20 (s, 1H), 5.23 (m, 2H), 5.08-4.95 (q, 2H), 3.46 (s, 3H). ! H-NMR (CDCI 3 d, ppm): 8.53 (d, 1H), 7.96 (dd, 1H), 7.72 (dt, 1H), 7.53 (dd, 1H), 7.49 (d, 1H), 7.30- 7.22 ( m, 2H), 6.99 (dd, 1H), 6.93 (d, 1H), 6.20 (s, 1H), 5.23 (m, 2H), 5.08-4.95 (q, 2H), 3.46 (s, 3H).
Beispiel Nr. 1.36-176 Example No. 1.36-176
'H-NMR (CDCI3 d, ppm) 7.78 (m, 1H), 7.41 (d, 1H), 7.14 (m, 1H), 6.91 (d, 1H), 6.33 (s, 1H), 4.97 (dd, 2H), 4.76 (s, 2H), 3.53 (s, 3H). 'H-NMR (CDCI 3 d, ppm) 7.78 (m, 1H), 7.41 (d, 1H), 7.14 (m, 1H), 6.91 (d, 1H), 6.33 (s, 1H), 4.97 (dd, 2H), 4.76 (s, 2H), 3.53 (s, 3H).
Beispiel Nr. F36-286 Example no.F36-286
!ff-NMR (CDCI3 d, ppm) 8.55 (m, 1H), 7.74 (m, 1H), 7.71-7.67 (m, 1H), 7.38 (d, 1H), 7.29 (m, 1H), 7.24-7.21 (m, 1H), 7.11 (m, 1H), 6.98 (d, 1H), 6.26 (s, 1H), 5.25 (s, 2H), 5.02 (dd, 2H), 3.50 (s, 3H). b) NMR-Peak-Listenverfahren ! ff-NMR (CDCl3 d, ppm) 8.55 (m, 1H), 7.74 (m, 1H), 7.71-7.67 (m, 1H), 7.38 (d, 1H), 7.29 (m, 1H), 7.24-7.21 ( m, 1H), 7.11 (m, 1H), 6.98 (d, 1H), 6.26 (s, 1H), 5.25 (s, 2H), 5.02 (dd, 2H), 3.50 (s, 3H). b) NMR peak list method
Die ' H-NMR-Datcn ausgewählter Beispiele können auch in Form von 'H-NMR- Peak listen notiert werden. Zu jedem Signalpeak wird erst der d-Wert in ppm und dann die Signalintensität in runden Klammem aufgeführt. Die d-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines Beispieles hat daher die Form: di (Intensität?: d2 (Intensität2); ; dί (Intensität ; ; dh (Intensitätn) The 'H-NMR data of selected examples can also be noted in the form of' H-NMR peak lists. For each signal peak, first the d-value in ppm and then the signal intensity is listed in round brackets. The d-value - signal intensity number pairs of different signal peaks are listed separated from each other by semicolons. The peak list of an example therefore has the form: di (intensity ?: d 2 (intensity2);; d ί (intensity ;; d h (intensityn)
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the real relationships between the signal intensities. Broad signals can have multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum. To calibrate the chemical shift of 1H-NMR spectra, we use tetramethylsilane and / or the chemical shift of the
Lösungsmittels, besondem im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak Vorkommen, muss es aber nicht. Die Listen der 'H-NMR- Peaks sind ähnlich den klassischen 'H-NMR-Aiisdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 'H-NMR-Aiisdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindun gen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 'H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von“Nebenprodukt- Fingerabdrücken” zu erkennen. Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD-Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak- Picking bei der klassischen lH-NMR-Interpretation. Weitere Details zu ^-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Solvent, especially in the case of spectra measured in DMSO. The tetramethylsilane peak can therefore appear in NMR peak lists, but does not have to be. The lists of 'H-NMR peaks are similar to the classic' H-NMR printouts and thus usually contain all peaks that are listed in a classic NMR interpretation. In addition, like classical 'H-NMR printouts, they can show solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities. When specifying connection signals in the delta range of solvents and / or water, our lists of 'H-NMR peaks show the usual solvent peaks, for example peaks from DMSO in DMSO-D 6 and the peak from water, which are usually have a high intensity on average. The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example, with a purity of> 90%). Such stereoisomers and / or impurities can be typical of the particular manufacturing process. Your peaks can thus help to identify the reproduction of our manufacturing process using “by-product fingerprints”. An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classical 1 H-NMR interpretation. Further details on ^ -NMR peak lists can be found in Research Disclosure Database Number 564025.
Beispiel Nr. 1.1-1: Example no. 1.1-1:
^-NMR^OO.O MHz, CDCL): 5= 8.0832 (1.2); 8.0787 (1.2); 8.0709 (1.2); 8.0664 (1.2); 7.6537 (1.2); 7.6492 (1.2); 7.6350 (1.4); 7.6305 (1.2); 7.3536 (1.8); 7.3311 (1.8); 7.2603 (75.4); 7.2524 (1.9); 7.2338 (1.8); 6.9368 (1.3); 6.9245 (1.3); 6.9181 (1.2); 6.9058 (1.2); 6.2898 (2.9); 4.9977 (0.8); 4.9579 (2.8); 4.9334 (2.8); 4.8936 (0.8); 4.2431 (0.8); 4.2387 (0.8); 4.2324 (1.5); 4.2258 (1.4); 4.2195 (0.9); 4.2150 (0.8); 3.5728 (1.9); 3.5620 (1.8); 3.5490 (1.7); 3.5066 (3.9); 3.5036 (3.9); 3.3484 (16.0); 1.5437 (2.3); 1.2596 (0.6); 0.8821 (0.9); 0.0080 (1.4); -0.0002 (45.2); -0.0085 (1.2) ^ -NMR ^ OO.O MHz, CDCL): 5 = 8.0832 (1.2); 8.0787 (1.2); 8.0709 (1.2); 8.0664 (1.2); 7.6537 (1.2); 7.6492 (1.2); 7.6350 (1.4); 7.6305 (1.2); 7.3536 (1.8); 7.3311 (1.8); 7.2603 (75.4); 7.2524 (1.9); 7.2338 (1.8); 6.9368 (1.3); 6.9245 (1.3); 6.9181 (1.2); 6.9058 (1.2); 6.2898 (2.9); 4.9977 (0.8); 4.9579 (2.8); 4.9334 (2.8); 4.8936 (0.8); 4.2431 (0.8); 4.2387 (0.8); 4.2324 (1.5); 4.2258 (1.4); 4.2195 (0.9); 4.2150 (0.8); 3.5728 (1.9); 3.5620 (1.8); 3.5490 (1.7); 3,5066 (3.9); 3,5036 (3.9); 3.3484 (16.0); 1.5437 (2.3); 1.2596 (0.6); 0.8821 (0.9); 0.0080 (1.4); -0.0002 (45.2); -0.0085 (1.2)
Beispiel Nr. 1.1-71: Example no. 1.1-71:
1H-NMR(400.0 MHz, CDCL): 5= 8.0782 (4.2); 8.0738 (4.5); 8.0659 (4.5); 8.0614 (4.4); 7.6474 (2.6); 7.6454 (2.9); 7.6430 (3.0); 7.6409 (2.8); 7.6287 (3.0); 7.6267 (3.2); 7.6243 (3.0); 7.6223 (2.8); 7.5193 (1.2); 7.3537 (7.5); 7.3312 (7.5); 7.2682 (8.4); 7.2605 (215.6); 7.2497 (7.6); 6.9964 (1.2); 6.9336 (5.2); 6.9212 (5.1); 6.9149 (5.0); 6.9026 (4.9); 6.2955 (6.4); 6.2897 (6.3); 5.0047 (1.9); 4.9945 (1.0); 4.9649 (5.7); 4.9548 (6.3); 4.9423 (6.3); 4.9300 (5.5); 4.9025 (1.1); 4.8902 (1.9); 4.1749 (1.5); 4.1661 (2.2); 4.1582 (1.6); 4.1483 (2.1); 4.1399 (3.8); 4.1334 (1.4); 4.1131 (1.1); 4.1083 (0.6); 4.0986 (1.2); 4.0917 (1.5); 4.0830 (1.4); 4.0742 (1.8); 4.0715 (2.0); 4.0663 (2.7); 4.0582 (1.7); 4.0447 (3.0); 4.0419 (2.2); 4.0294 (1.6); 4.0181 (1.8); 4.0028 (1.2); 3.8697 (0.8); 3.8662 (0.8); 3.8526 (1.6); 3.8489 (2.4); 3.8453 (1.4); 3.8322 (2.6); 3.8156 (1.4); 3.7948 (1.0); 3.7878 (1.0); 3.7777 (1.9); 3.7705 (1.9); 3.7613 (1.3); 3.7545 (1.4); 3.7403 (0.6); 3.7332 (0.6); 3.5073 (15.8); 3.5048 (16.0); 2.0452 (3.5); 1.9850 (0.6); 1.9685 (0.9); 1.9522 (1.4); 1.9438 (1.1); 1.9398 (1.0); 1.9317 (0.9); 1.9196 (1.8); 1.9158 (1.6); 1.9012 (2.9); 1.8850 (3.6); 1.8820 (3.5); 1.8655 (2.2); 1.8499 (0.8); 1.6072 (0.8); 1.5914 (1.4); 1.5746 (1.7); 1.5684 (1.4); 1.5499 (4.4); 1.3032 (0.9); 1.2844 (1.5); 1.2773 (2.2); 1.2642 (4.4); 1.2597 (5.1); 1.2416 (1.5); 0.8988 (2.3); 0.8820 (7.9); 0.8643 (3.1); 0.0080 (3.8); -0.0002 (129.8); -0.0085 (3.6) 1 H-NMR (400.0 MHz, CDCL): 5 = 8.0782 (4.2); 8.0738 (4.5); 8.0659 (4.5); 8.0614 (4.4); 7.6474 (2.6); 7.6454 (2.9); 7.6430 (3.0); 7.6409 (2.8); 7.6287 (3.0); 7.6267 (3.2); 7.6243 (3.0); 7.6223 (2.8); 7.5193 (1.2); 7.3537 (7.5); 7.3312 (7.5); 7.2682 (8.4); 7.2605 (215.6); 7.2497 (7.6); 6.9964 (1.2); 6.9336 (5.2); 6.9212 (5.1); 6.9149 (5.0); 6.9026 (4.9); 6.2955 (6.4); 6.2897 (6.3); 5,0047 (1.9); 4.9945 (1.0); 4.9649 (5.7); 4.9548 (6.3); 4.9423 (6.3); 4.9300 (5.5); 4.9025 (1.1); 4.8902 (1.9); 4.1749 (1.5); 4.1661 (2.2); 4.1582 (1.6); 4.1483 (2.1); 4.1399 (3.8); 4.1334 (1.4); 4.1131 (1.1); 4.1083 (0.6); 4.0986 (1.2); 4.0917 (1.5); 4.0830 (1.4); 4.0742 (1.8); 4.0715 (2.0); 4.0663 (2.7); 4.0582 (1.7); 4.0447 (3.0); 4.0419 (2.2); 4.0294 (1.6); 4.0181 (1.8); 4.0028 (1.2); 3.8697 (0.8); 3.8662 (0.8); 3.8526 (1.6); 3.8489 (2.4); 3.8453 (1.4); 3.8322 (2.6); 3.8156 (1.4); 3.7948 (1.0); 3.7878 (1.0); 3.7777 (1.9); 3.7705 (1.9); 3.7613 (1.3); 3.7545 (1.4); 3.7403 (0.6); 3.7332 (0.6); 3,5073 (8/15); 3,5048 (16.0); 2.0452 (3.5); 1.9850 (0.6); 1.9685 (0.9); 1.9522 (1.4); 1.9438 (1.1); 1.9398 (1.0); 1.9317 (0.9); 1.9196 (1.8); 1.9158 (1.6); 1.9012 (2.9); 1.8850 (3.6); 1.8820 (3.5); 1.8655 (2.2); 1.8499 (0.8); 1.6072 (0.8); 1.5914 (1.4); 1.5746 (1.7); 1.5684 (1.4); 1.5499 (4.4); 1.3032 (0.9); 1.2844 (1.5); 1.2773 (2.2); 1.2642 (4.4); 1.2597 (5.1); 1.2416 (1.5); 0.8988 (2.3); 0.8820 (7.9); 0.8643 (3.1); 0.0080 (3.8); -0.0002 (129.8); -0.0085 (3.6)
Beispiel Nr. 1.1-72: Example no. 1.1-72:
1H-NMR(400.0 MHz, CDC13): d= 8.3787 (3.2); 8.3747 (3.3); 8.3668 (3.4); 8.3626 (3.3); 7.6161 (2.7); 7.6120 (2.7); 7.5969 (3.0); 7.5929 (2.8); 7.5194 (0.8); 7.3712 (5.4); 7.3488 (5.4); 7.2605 (145.8); 7.0431 1 H-NMR (400.0 MHz, CDC1 3): d = 8.3787 (3.2); 8.3747 (3.3); 8.3668 (3.4); 8.3626 (3.3); 7.6161 (2.7); 7.6120 (2.7); 7.5969 (3.0); 7.5929 (2.8); 7.5194 (0.8); 7.3712 (5.4); 7.3488 (5.4); 7.2605 (145.8); 7.0431
(3.4); 7.0310 (3.4); 7.0238 (3.1); 7.0118 (3.1); 6.9964 (0.8); 6.9610 (2.9); 6.9581 (2.9); 6.9428 (2.9); 6.9398 (2.8); 6.2954 (7.1); 4.1487 (1.2); 4.1326 (1.3); 4.1212 (2.0); 4.1092 (1.7); 4.1061 (1.6); 4.0934(3.4); 7.0310 (3.4); 7.0238 (3.1); 7.0118 (3.1); 6.9964 (0.8); 6.9610 (2.9); 6.9581 (2.9); 6.9428 (2.9); 6.9398 (2.8); 6.2954 (7.1); 4.1487 (1.2); 4.1326 (1.3); 4.1212 (2.0); 4.1092 (1.7); 4,1061 (1.6); 4.0934
(1.5); 4.0140 (1.5); 3.9968 (1.8); 3.9872 (1.1); 3.9766 (1.6); 3.9698 (1.5); 3.9496 (1.2); 3.9270 (16.0); 3.8336 (0.9); 3.8201 (1.0); 3.8129 (2.0); 3.7992 (2.0); 3.7923 (1.4); 3.7787 (1.4); 3.7625 (1.2); 3.7566 (1.2); 3.7446 (1.5); 3.7393 (3.1); 3.7217 (2.9); 3.7010 (1.9); 3.6806 (0.9); 3.5046 (15.4); 3.4912 (2.8); 3.4828 (2.2); 3.4691 (2.2); 2.5756 (0.9); 2.5597 (1.1); 2.5411 (0.9); 2.0451 (2.5); 2.0275 (0.6); 2.0137 (0.7); 2.0081 (0.9); 1.9952 (1.2); 1.9869 (0.7); 1.9826 (0.8); 1.9738 (1.1); 1.9622 (1.0); 1.9558 (0.6); 1.9416 (0.6); 1.6146 (0.7); 1.5957 (1.6); 1.5637 (4.8); 1.2773 (1.2); 1.2596 (2.6); 1.2415 (0.8); 0.8988 (1.0); 0.8821 (2.5); 0.8642 (1.0); 0.0079 (3.2); -0.0002 (83.2); -0.0085 (2.6) (1.5); 4.0140 (1.5); 3.9968 (1.8); 3.9872 (1.1); 3.9766 (1.6); 3.9698 (1.5); 3,9496 (1.2); 3.9270 (16.0); 3.8336 (0.9); 3.8201 (1.0); 3.8129 (2.0); 3.7992 (2.0); 3.7923 (1.4); 3.7787 (1.4); 3.7625 (1.2); 3.7566 (1.2); 3.7446 (1.5); 3.7393 (3.1); 3.7217 (2.9); 3.7010 (1.9); 3.6806 (0.9); 3,5046 (15.4); 3.4912 (2.8); 3.4828 (2.2); 3.4691 (2.2); 2.5756 (0.9); 2.5597 (1.1); 2.5411 (0.9); 2.0451 (2.5); 2.0275 (0.6); 2.0137 (0.7); 2.0081 (0.9); 1.9952 (1.2); 1.9869 (0.7); 1.9826 (0.8); 1.9738 (1.1); 1.9622 (1.0); 1.9558 (0.6); 1.9416 (0.6); 1.6146 (0.7); 1.5957 (1.6); 1.5637 (4.8); 1.2773 (1.2); 1.2596 (2.6); 1.2415 (0.8); 0.8988 (1.0); 0.8821 (2.5); 0.8642 (1.0); 0.0079 (3.2); -0.0002 (83.2); -0.0085 (2.6)
Beispiel Nr. 1.10-1 : Example no. 1.10-1:
1H-NMR(400.0 MHz, CDC13): d= 8.3904 (1.2); 8.3863 (1.2); 8.3784 (1.3); 8.3743 (1.2); 7.6278 (1.2); 7.6236 (1.2); 7.6086 (1.4); 7.6045 (1.3); 7.3619 (2.0); 7.3395 (2.0); 7.2605 (44.2); 7.0349 (1.3); 7.0229 (1.3); 7.0157 (1.2); 7.0038 (1.2); 6.9348 (1.8); 6.9166 (1.8); 6.2894 (3.2); 4.2524 (1.6); 4.2412 (1.4); 4.2374 (1.1); 4.2288 (1.8); 3.9761 (7.6); 3.5802 (2.1); 3.5739 (0.7); 3.5712 (1.1); 3.5683 (1.9); 3.5566 (1.9); 3.5043 (4.5); 3.5015 (4.5); 3.3425 (16.0); 1.5626 (1.0); 1.2595 (0.7); 0.8821 (0.8); 0.0079 (0.8); - 0.0002 (25.1); -0.0085 (0.8) 1 H-NMR (400.0 MHz, CDC1 3): d = 8.3904 (1.2); 8.3863 (1.2); 8.3784 (1.3); 8.3743 (1.2); 7.6278 (1.2); 7.6236 (1.2); 7.6086 (1.4); 7.6045 (1.3); 7.3619 (2.0); 7.3395 (2.0); 7.2605 (44.2); 7.0349 (1.3); 7.0229 (1.3); 7.0157 (1.2); 7.0038 (1.2); 6.9348 (1.8); 6.9166 (1.8); 6.2894 (3.2); 4.2524 (1.6); 4.2412 (1.4); 4.2374 (1.1); 4.2288 (1.8); 3.9761 (7.6); 3.5802 (2.1); 3.5739 (0.7); 3.5712 (1.1); 3.5683 (1.9); 3.5566 (1.9); 3,5043 (4.5); 3,5015 (4.5); 3.3425 (16.0); 1.5626 (1.0); 1.2595 (0.7); 0.8821 (0.8); 0.0079 (0.8); - 0.0002 (25.1); -0.0085 (0.8)
Beispiel Nr. 1.10-26: Example no. 1.10-26:
1H-NMR(400.0 MHz, CDC13): d= 8.3833 (1.8); 8.3796 (1.8); 8.3715 (1.8); 7.6166 (1.8); 7.6131 (1.6); 7.5974 (1.8); 7.5939 (1.6); 7.3661 (2.5); 7.3437 (2.4); 7.2610 (18.3); 7.0345 (1.6); 7.0225 (1.6); 7.0155 1 H-NMR (400.0 MHz, CDCl 3 ): d = 8.3833 (1.8); 8.3796 (1.8); 8.3715 (1.8); 7.6166 (1.8); 7.6131 (1.6); 7.5974 (1.8); 7.5939 (1.6); 7.3661 (2.5); 7,3437 (2.4); 7.2610 (18.3); 7.0345 (1.6); 7.0225 (1.6); 7.0155
(1.5); 7.0035 (1.4); 6.9688 (2.3); 6.9507 (2.3); 6.2963 (4.5); 4.1962 (2.4); 4.1802 (4.5); 4.1642 (2.3); 3.9380 (8.9); 3.5065 (8.9); 3.4117 (2.7); 3.3961 (5.0); 3.3804 (2.6); 3.2978 (16.0); 1.9106 (0.8); 1.8950(1.5); 7.0035 (1.4); 6.9688 (2.3); 6.9507 (2.3); 6.2963 (4.5); 4.1962 (2.4); 4.1802 (4.5); 4.1642 (2.3); 3.9380 (8.9); 3,5065 (8.9); 3.4117 (2.7); 3.3961 (5.0); 3.3804 (2.6); 3.2978 (16.0); 1.9106 (0.8); 1.8950
(2.6); 1.8791 (3.6); 1.8632 (2.4); 1.8474 (0.7); 1.5720 (1.0); 1.2562 (0.9); -0.0002 (10.6) Beispiel Nr. 1.10-71: (2.6); 1.8791 (3.6); 1.8632 (2.4); 1.8474 (0.7); 1.5720 (1.0); 1.2562 (0.9); -0.0002 (10.6) Example no.1.10-71:
1H-NMR(400.0 MHz, CDC13): d= 8.3861 (4.4); 8.3819 (4.5); 8.3741 (4.7); 8.3700 (4.4); 7.6193 (4.1); 7.6151 (4.1); 7.6001 (4.5); 7.5960 (4.2); 7.3625 (7.0); 7.3401 (7.0); 7.2613 (71.1); 7.0311 (4.7); 7.0192 1 H-NMR (400.0 MHz, CDC1 3): d = 8.3861 (4.4); 8.3819 (4.5); 8.3741 (4.7); 8.3700 (4.4); 7.6193 (4.1); 7.6151 (4.1); 7,6001 (4.5); 7.5960 (4.2); 7.3625 (7.0); 7.3401 (7.0); 7.2613 (71.1); 7.0311 (4.7); 7.0192
(4.6); 7.0120 (4.4); 7.0000 (4.4); 6.9498 (5.2); 6.9316 (5.2); 6.2929 (6.5); 6.2899 (6.2); 4.1877 (1.7); 4.1859 (1.6); 4.1788 (2.2); 4.1604 (2.3); 4.1515 (3.7); 4.1344 (0.6); 4.1178 (1.6); 4.1090 (1.1); 4.1009(4.6); 7.0120 (4.4); 7.0000 (4.4); 6.9498 (5.2); 6.9316 (5.2); 6.2929 (6.5); 6.2899 (6.2); 4.1877 (1.7); 4.1859 (1.6); 4.1788 (2.2); 4.1604 (2.3); 4.1515 (3.7); 4.1344 (0.6); 4.1178 (1.6); 4.1090 (1.1); 4.1009
(1.7); 4.0926 (1.6); 4.0837 (0.8); 4.0758 (0.9); 4.0600 (2.8); 4.0510 (2.7); 4.0449 (1.5); 4.0353 (2.0); 4.0331 (2.0); 4.0238 (2.2); 4.0179 (1.2); 4.0083 (1.2); 3.9848 (9.0); 3.9828 (9.4); 3.9797 (12.9); 3.9389 (0.8); 3.8776 (1.4); 3.8607 (2.4); 3.8566 (2.4); 3.8441 (1.6); 3.8401 (3.1); 3.8236 (1.7); 3.7976 (1.0); 3.7946 (1.0); 3.7797 (2.2); 3.7770 (2.0); 3.7595 (1.7); 3.7434 (0.6); 3.5057 (16.0); 3.5028 (15.6); 1.9867 (0.7); 1.9840 (0.7); 1.9738 (0.7); 1.9703 (1.1); 1.9661 (1.0); 1.9621 (0.8); 1.9530 (1.1); 1.9487 (1.2); 1.9410 (1.2); 1.9373 (1.0); 1.9268 (1.4); 1.9202 (1.6); 1.9121 (1.6); 1.9020 (2.4); 1.8925 (1.8); 1.8850 (2.4); 1.8802 (1.8); 1.8642 (1.5); 1.8476 (0.6); 1.6307 (0.6); 1.6222 (0.6); 1.6132 (1.0); 1.6050 (1.3); 1.6005 (1.4); 1.5917 (2.0); 1.5879 (1.8); 1.5831 (2.6); 1.5748 (2.2); 1.5657 (1.6); 1.5563 (1.1); 1.3333 (0.7); 1.2845 (1.0); 1.2555 (1.3); 1.1078 (0.6); 0.0080 (1.5); -0.0002 (41.8); -0.0085 (1.2) (1.7); 4.0926 (1.6); 4.0837 (0.8); 4.0758 (0.9); 4.0600 (2.8); 4.0510 (2.7); 4.0449 (1.5); 4.0353 (2.0); 4.0331 (2.0); 4.0238 (2.2); 4.0179 (1.2); 4.0083 (1.2); 3.9848 (9.0); 3.9828 (9.4); 3,9797 (12.9); 3.9389 (0.8); 3.8776 (1.4); 3.8607 (2.4); 3.8566 (2.4); 3.8441 (1.6); 3.8401 (3.1); 3.8236 (1.7); 3.7976 (1.0); 3.7946 (1.0); 3.7797 (2.2); 3.7770 (2.0); 3.7595 (1.7); 3.7434 (0.6); 3,5057 (16.0); 3,5028 (15.6); 1.9867 (0.7); 1.9840 (0.7); 1.9738 (0.7); 1.9703 (1.1); 1.9661 (1.0); 1.9621 (0.8); 1.9530 (1.1); 1.9487 (1.2); 1.9410 (1.2); 1.9373 (1.0); 1.9268 (1.4); 1.9202 (1.6); 1.9121 (1.6); 1.9020 (2.4); 1.8925 (1.8); 1.8850 (2.4); 1.8802 (1.8); 1.8642 (1.5); 1.8476 (0.6); 1.6307 (0.6); 1.6222 (0.6); 1.6132 (1.0); 1.6050 (1.3); 1.6005 (1.4); 1.5917 (2.0); 1.5879 (1.8); 1.5831 (2.6); 1.5748 (2.2); 1.5657 (1.6); 1.5563 (1.1); 1.3333 (0.7); 1.2845 (1.0); 1.2555 (1.3); 1.1078 (0.6); 0.0080 (1.5); -0.0002 (41.8); -0.0085 (1.2)
Beispiel Nr. 1.10-72: Example no.1.10-72:
1H-NMR(400.0 MHz, CDC13): d= 8.3787 (3.2); 8.3747 (3.3); 8.3668 (3.4); 8.3626 (3.3); 7.6161 (2.7); 7.6120 (2.7); 7.5969 (3.0); 7.5929 (2.8); 7.5194 (0.8); 7.3712 (5.4); 7.3488 (5.4); 7.2605 (145.8); 7.0431 1 H-NMR (400.0 MHz, CDC1 3): d = 8.3787 (3.2); 8.3747 (3.3); 8.3668 (3.4); 8.3626 (3.3); 7.6161 (2.7); 7.6120 (2.7); 7.5969 (3.0); 7.5929 (2.8); 7.5194 (0.8); 7.3712 (5.4); 7.3488 (5.4); 7.2605 (145.8); 7.0431
(3.4); 7.0310 (3.4); 7.0238 (3.1); 7.0118 (3.1); 6.9964 (0.8); 6.9610 (2.9); 6.9581 (2.9); 6.9428 (2.9); 6.9398 (2.8); 6.2954 (7.1); 4.1487 (1.2); 4.1326 (1.3); 4.1212 (2.0); 4.1092 (1.7); 4.1061 (1.6); 4.0934(3.4); 7.0310 (3.4); 7.0238 (3.1); 7.0118 (3.1); 6.9964 (0.8); 6.9610 (2.9); 6.9581 (2.9); 6.9428 (2.9); 6.9398 (2.8); 6.2954 (7.1); 4.1487 (1.2); 4.1326 (1.3); 4.1212 (2.0); 4.1092 (1.7); 4,1061 (1.6); 4.0934
(1.5); 4.0140 (1.5); 3.9968 (1.8); 3.9872 (1.1); 3.9766 (1.6); 3.9698 (1.5); 3.9496 (1.2); 3.9270 (16.0); 3.8336 (0.9); 3.8201 (1.0); 3.8129 (2.0); 3.7992 (2.0); 3.7923 (1.4); 3.7787 (1.4); 3.7625 (1.2); 3.7566 (1.2); 3.7446 (1.5); 3.7393 (3.1); 3.7217 (2.9); 3.7010 (1.9); 3.6806 (0.9); 3.5046 (15.4); 3.4912 (2.8); 3.4828 (2.2); 3.4691 (2.2); 2.5756 (0.9); 2.5597 (1.1); 2.5411 (0.9); 2.0451 (2.5); 2.0275 (0.6); 2.0137 (0.7); 2.0081 (0.9); 1.9952 (1.2); 1.9869 (0.7); 1.9826 (0.8); 1.9738 (1.1); 1.9622 (1.0); 1.9558 (0.6); 1.9416 (0.6); 1.6146 (0.7); 1.5957 (1.6); 1.5637 (4.8); 1.2773 (1.2); 1.2596 (2.6); 1.2415 (0.8); 0.8988 (1.0); 0.8821 (2.5); 0.8642 (1.0); 0.0079 (3.2); -0.0002 (83.2); -0.0085 (2.6) (1.5); 4.0140 (1.5); 3.9968 (1.8); 3.9872 (1.1); 3.9766 (1.6); 3.9698 (1.5); 3,9496 (1.2); 3.9270 (16.0); 3.8336 (0.9); 3.8201 (1.0); 3.8129 (2.0); 3.7992 (2.0); 3.7923 (1.4); 3.7787 (1.4); 3.7625 (1.2); 3.7566 (1.2); 3.7446 (1.5); 3.7393 (3.1); 3.7217 (2.9); 3.7010 (1.9); 3.6806 (0.9); 3,5046 (15.4); 3.4912 (2.8); 3.4828 (2.2); 3.4691 (2.2); 2.5756 (0.9); 2.5597 (1.1); 2.5411 (0.9); 2.0451 (2.5); 2.0275 (0.6); 2.0137 (0.7); 2.0081 (0.9); 1.9952 (1.2); 1.9869 (0.7); 1.9826 (0.8); 1.9738 (1.1); 1.9622 (1.0); 1.9558 (0.6); 1.9416 (0.6); 1.6146 (0.7); 1.5957 (1.6); 1.5637 (4.8); 1.2773 (1.2); 1.2596 (2.6); 1.2415 (0.8); 0.8988 (1.0); 0.8821 (2.5); 0.8642 (1.0); 0.0079 (3.2); -0.0002 (83.2); -0.0085 (2.6)
Beispiel Nr. 1.10-115: Example no.1.10-115:
1H-NMR(400.0 MHz, CDC13): d= 8.3922 (2.9); 8.3881 (2.8); 8.3802 (3.0); 8.3761 (2.7); 7.6202 (2.6); 7.6161 (2.6); 7.6010 (2.9); 7.5969 (2.7); 7.3767 (4.8); 7.3543 (4.8); 7.2606 (39.3); 7.0575 (3.0); 7.0455 1 H-NMR (400.0 MHz, CDC1 3): d = 8.3922 (2.9); 8.3881 (2.8); 8.3802 (3.0); 8.3761 (2.7); 7.6202 (2.6); 7.6161 (2.6); 7.6010 (2.9); 7.5969 (2.7); 7.3767 (4.8); 7.3543 (4.8); 7.2606 (39.3); 7.0575 (3.0); 7.0455
(2.8); 7.0383 (2.8); 7.0263 (2.6); 6.9318 (4.2); 6.9136 (4.2); 6.3121 (0.6); 6.3078 (0.7); 6.2980 (6.8);(2.8); 7.0383 (2.8); 7.0263 (2.6); 6.9318 (4.2); 6.9136 (4.2); 6.3121 (0.6); 6.3078 (0.7); 6.2980 (6.8);
5.4498 (1.1); 5.4471 (1.1); 5.4340 (2.2); 5.4208 (1.2); 5.4181 (1.2); 5.4050 (0.6); 4.8709 (2.5); 4.85235,4498 (1.1); 5,4471 (1.1); 5.4340 (2.2); 5,4208 (1.2); 5.4181 (1.2); 5.4050 (0.6); 4.8709 (2.5); 4.8523
(4.0); 4.8339 (2.7); 4.6447 (2.6); 4.6315 (2.6); 4.6286 (2.4); 4.6259 (2.2); 4.6125 (2.0); 3.9469 (16.0);(4.0); 4.8339 (2.7); 4.6447 (2.6); 4.6315 (2.6); 4.6286 (2.4); 4.6259 (2.2); 4.6125 (2.0); 3,9469 (16.0);
3.9379 (0.8); 3.9306 (1.3); 3.5409 (0.8); 3.5269 (0.5); 3.5110 (11.4); 3.5081 (10.8); 1.5532 (0.9); 1.2546 (2.2); 1.2321 (0.7); 0.0080 (1.4); -0.0002 (51.6); -0.0085 (1.5) Beispiel Nr. 1.10-176: 3.9379 (0.8); 3,9306 (1.3); 3.5409 (0.8); 3.5269 (0.5); 3.5110 (11.4); 3,5081 (10.8); 1.5532 (0.9); 1.2546 (2.2); 1.2321 (0.7); 0.0080 (1.4); -0.0002 (51.6); -0.0085 (1.5) Example no. 1.10-176:
1H-NMR(400.0 MHz, CDC13): 5= 8.4351 (2.5); 8.4310 (2.5); 8.4230 (2.6); 8.4189 (2.5); 7.6834 (2.5); 7.6793 (2.5); 7.6642 (2.7); 7.6601 (2.6); 7.3732 (4.0); 7.3509 (4.0); 7.2603 (85.1); 7.0863 (2.6); 7.0742 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 8.4351 (2.5); 8.4310 (2.5); 8.4230 (2.6); 8.4189 (2.5); 7.6834 (2.5); 7.6793 (2.5); 7.6642 (2.7); 7.6601 (2.6); 7.3732 (4.0); 7.3509 (4.0); 7.2603 (85.1); 7.0863 (2.6); 7.0742
(2.6); 7.0671 (2.5); 7.0550 (2.4); 6.8332 (3.6); 6.8151 (3.6); 6.2986 (6.6); 4.7467 (16.0); 4.1309 (0.8); 4.1130 (0.8); 3.9803 (0.9); 3.9396 (7.6); 3.9306 (7.6); 3.8899 (0.9); 3.5099 (9.8); 3.5071 (9.9); 2.0450(2.6); 7.0671 (2.5); 7.0550 (2.4); 6.8332 (3.6); 6.8151 (3.6); 6.2986 (6.6); 4,7467 (16.0); 4.1309 (0.8); 4.1130 (0.8); 3.9803 (0.9); 3,9396 (7.6); 3,9306 (7.6); 3.8899 (0.9); 3,5099 (9.8); 3,5071 (9.9); 2.0450
(3.7); 1.5506 (1.0); 1.2772 (1.3); 1.2594 (2.7); 1.2415 (1.1); 0.8989 (0.5); 0.8820 (1.5); 0.8642 (0.6); 0.0079 (1.9); -0.0002 (50.7); -0.0085 (1.8) (3.7); 1.5506 (1.0); 1.2772 (1.3); 1.2594 (2.7); 1.2415 (1.1); 0.8989 (0.5); 0.8820 (1.5); 0.8642 (0.6); 0.0079 (1.9); -0.0002 (50.7); -0.0085 (1.8)
Beispiel Nr. 1.14-2: Example no.1.14-2:
1H-NMR(400.0 MHz, CDC13): 5= 7.9990 (0.7); 7.9949 (0.7); 7.9866 (0.8); 7.9826 (0.7); 7.8814 (1.0); 7.8600 (1.0); 7.5167 (0.7); 7.5127 (0.7); 7.4973 (0.8); 7.4932 (0.8); 7.2613 (38.0); 7.1365 (1.0); 7.1216 (1.0); 7.0022 (0.8); 6.9899 (0.8); 6.9828 (0.8); 6.9704 (0.7); 6.2800 (2.0); 4.9673 (0.7); 4.9275 (1.6); 4.8679 (1.6); 4.8280 (0.7); 4.1333 (0.8); 4.1280 (0.8); 4.1154 (0.9); 4.1103 (0.8); 3.5016 (2.8); 3.4988 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9990 (0.7); 7.9949 (0.7); 7.9866 (0.8); 7.9826 (0.7); 7.8814 (1.0); 7,8600 (1.0); 7.5167 (0.7); 7.5127 (0.7); 7.4973 (0.8); 7.4932 (0.8); 7.2613 (38.0); 7.1365 (1.0); 7.1216 (1.0); 7.0022 (0.8); 6.9899 (0.8); 6.9828 (0.8); 6.9704 (0.7); 6,2800 (2.0); 4.9673 (0.7); 4.9275 (1.6); 4,8679 (1.6); 4.8280 (0.7); 4.1333 (0.8); 4.1280 (0.8); 4.1154 (0.9); 4.1103 (0.8); 3,5016 (2.8); 3.4988
(2.8); 1.5546 (16.0); 1.2673 (2.1); 1.2495 (4.4); 1.2316 (2.0); 0.0080 (0.6); -0.0002 (22.3); -0.0085 (0.6) (2.8); 1.5546 (16.0); 1.2673 (2.1); 1.2495 (4.4); 1.2316 (2.0); 0.0080 (0.6); -0.0002 (22.3); -0.0085 (0.6)
Beispiel Nr. 1.14-23: Example no.1.14-23:
^-NMR^OO.O MHz, CDCI3): 5= 7.9951 (2.2); 7.9926 (2.3); 7.9869 (2.3); 7.9844 (2.3); 7.8763 (3.2); 7.8620 (3.2); 7.5115 (2.2); 7.5090 (2.3); 7.4986 (2.4); 7.4961 (2.3); 7.2615 (13.0); 7.1335 (3.0); 7.1236 (3.0); 6.9959 (2.2); 6.9876 (2.2); 6.9829 (2.1); 6.9747 (2.0); 6.2797 (6.7); 5.2994 (2.0); 4.9573 (2.7); 4.9308 (4.6); 4.8640 (4.6); 4.8375 (2.6); 4.1494 (0.5); 4.1436 (0.8); 4.1367 (1.2); 4.1316 (2.4); 4.1246 (2.6); 4.1197 (2.6); 4.1127 (2.5); 4.1075 (1.2); 4.1008 (0.8); 4.0948 (0.4); 3.4998 (12.0); 2.1710 (0.5); 2.0445 (2.1); 1.5652 (50.0); 1.3012 (0.5); 1.2900 (0.6); 1.2800 (0.6); 1.2709 (1.3); 1.2608 (7.3); 1.2489 (12.4); 1.2370 (6.0); 0.8935 (1.2); 0.8821 (2.6); 0.8701 (1.3); -0.0001 (0.6) ^ -NMR ^ OO.O MHz, CDCI3): 5 = 7.9951 (2.2); 7.9926 (2.3); 7.9869 (2.3); 7.9844 (2.3); 7.8763 (3.2); 7.8620 (3.2); 7.5115 (2.2); 7.5090 (2.3); 7.4986 (2.4); 7.4961 (2.3); 7.2615 (13.0); 7.1335 (3.0); 7.1236 (3.0); 6.9959 (2.2); 6.9876 (2.2); 6.9829 (2.1); 6.9747 (2.0); 6.2797 (6.7); 5,2994 (2.0); 4.9573 (2.7); 4,9308 (4.6); 4.8640 (4.6); 4.8375 (2.6); 4.1494 (0.5); 4.1436 (0.8); 4.1367 (1.2); 4.1316 (2.4); 4.1246 (2.6); 4.1197 (2.6); 4.1127 (2.5); 4.1075 (1.2); 4.1008 (0.8); 4.0948 (0.4); 3.4998 (12.0); 2.1710 (0.5); 2.0445 (2.1); 1.5652 (50.0); 1.3012 (0.5); 1.2900 (0.6); 1.2800 (0.6); 1.2709 (1.3); 1.2608 (7.3); 1.2489 (12.4); 1.2370 (6.0); 0.8935 (1.2); 0.8821 (2.6); 0.8701 (1.3); -0.0001 (0.6)
Beispiel Nr. 1.14-422: Example no.1.14-422:
1H-NMR(400.0 MHz, CDCI3): 5= 9.3524 (0.6); 7.9993 (1.1); 7.9951 (1.1); 7.9869 (1.2); 7.9828 (1.1); 7.8815 (1.4); 7.8602 (1.4); 7.5169 (1.1); 7.5128 (0.9); 7.4974 (1.2); 7.4936 (1.1); 7.2606 (47.9); 7.1371 1 H-NMR (400.0 MHz, CDCl3): 5 = 9.3524 (0.6); 7.9993 (1.1); 7.9951 (1.1); 7.9869 (1.2); 7.9828 (1.1); 7.8815 (1.4); 7.8602 (1.4); 7.5169 (1.1); 7.5128 (0.9); 7.4974 (1.2); 7.4936 (1.1); 7.2606 (47.9); 7.1371
(1.3); 7.1222 (1.4); 7.0020 (1.0); 6.9896 (1.2); 6.9825 (1.0); 6.9704 (1.0); 6.2797 (2.7); 4.9679 (1.1);(1.3); 7.1222 (1.4); 7.0020 (1.0); 6.9896 (1.2); 6.9825 (1.0); 6.9704 (1.0); 6.2797 (2.7); 4,9679 (1.1);
4.9281 (2.2); 4.8677 (2.2); 4.8278 (1.1); 4.1330 (1.2); 4.1276 (1.3); 4.1148 (1.3); 4.1097 (1.2); 3.50164.9281 (2.2); 4.8677 (2.2); 4.8278 (1.1); 4.1330 (1.2); 4.1276 (1.3); 4.1148 (1.3); 4.1097 (1.2); 3,5016
(4.4); 1.5456 (16.0); 1.2672 (2.8); 1.2494 (5.7); 1.2315 (2.7); 0.0079 (3.3); -0.0002 (50.9) (4.4); 1.5456 (16.0); 1.2672 (2.8); 1.2494 (5.7); 1.2315 (2.7); 0.0079 (3.3); -0.0002 (50.9)
Beispiel Nr. 1.15-1: Example no.1.15-1:
1H-NMR(400.0 MHz, CDC13): 5= 7.9244 (1.5); 7.9208 (1.4); 7.9122 (1.6); 7.9085 (1.4); 7.3766 (2.3); 7.3545 (2.3); 7.3351 (1.5); 7.3314 (1.4); 7.3157 (1.7); 7.3120 (1.4); 7.2603 (13.9); 6.9412 (1.4); 6.9288 (1.5); 6.9217 (1.5); 6.9147 (2.4); 6.9094 (1.5); 6.8984 (2.2); 6.2869 (4.2); 5.0204 (1.1); 4.9806 (3.6); 4.9480 (3.5); 4.9082 (1.1); 4.2528 (1.2); 4.2474 (1.4); 4.2421 (2.2); 4.2349 (2.2); 4.2294 (1.4); 4.2241 (1.2); 3.5455 (2.5); 3.5340 (3.8); 3.5220 (2.4); 3.5032 (7.5); 3.3128 (16.0); 1.5779 (0.6); 1.2652 (0.8); 0.8821 (0.8); -0.0002 (15.5) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9244 (1.5); 7.9208 (1.4); 7.9122 (1.6); 7.9085 (1.4); 7.3766 (2.3); 7.3545 (2.3); 7.3351 (1.5); 7.3314 (1.4); 7.3157 (1.7); 7.3120 (1.4); 7.2603 (13.9); 6.9412 (1.4); 6.9288 (1.5); 6.9217 (1.5); 6.9147 (2.4); 6.9094 (1.5); 6.8984 (2.2); 6.2869 (4.2); 5.0204 (1.1); 4,9806 (3.6); 4.9480 (3.5); 4.9082 (1.1); 4.2528 (1.2); 4.2474 (1.4); 4.2421 (2.2); 4.2349 (2.2); 4.2294 (1.4); 4.2241 (1.2); 3.5455 (2.5); 3.5340 (3.8); 3.5220 (2.4); 3,5032 (7.5); 3.3128 (16.0); 1.5779 (0.6); 1.2652 (0.8); 0.8821 (0.8); -0.0002 (15.5)
Beispiel Nr. 1.15-6: Example no.1.15-6:
1H-NMR(400.0 MHz, CDC13): 5= 7.8993 (2.4); 7.8875 (2.6); 7.3746 (3.4); 7.3521 (3.9); 7.3422 (3.5); 7.3251 (5.9); 7.3065 (9.2); 7.2598 (59.3); 6.9252 (2.2); 6.9124 (4.7); 6.8947 (4.8); 6.2696 (6.3); 5.0238 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.8993 (2.4); 7.8875 (2.6); 7.3746 (3.4); 7.3521 (3.9); 7.3422 (3.5); 7.3251 (5.9); 7.3065 (9.2); 7.2598 (59.3); 6.9252 (2.2); 6.9124 (4.7); 6.8947 (4.8); 6.2696 (6.3); 5.0238
(1.6); 4.9842 (5.3); 4.9545 (5.4); 4.9141 (1.6); 4.5134 (12.4); 4.2951 (3.4); 4.2833 (4.2); 4.2719 (3.4); 3.6576 (3.6); 3.6457 (4.3); 3.6337 (3.2); 3.4829 (12.3); 1.5365 (16.0); 1.2650 (2.2); 0.8826 (2.1); 0.8649 (1.0); -0.0002 (80.1) (1.6); 4.9842 (5.3); 4.9545 (5.4); 4.9141 (1.6); 4.5134 (12.4); 4.2951 (3.4); 4.2833 (4.2); 4.2719 (3.4); 3.6576 (3.6); 3.6457 (4.3); 3.6337 (3.2); 3.4829 (12.3); 1,5365 (16.0); 1.2650 (2.2); 0.8826 (2.1); 0.8649 (1.0); -0.0002 (80.1)
Beispiel Nr. 1.15-23: Example no.1.15-23:
1H-NMR(400.0 MHz, CDC13): 5= 7.9176 (1.2); 7.9136 (1.3); 7.9053 (1.3); 7.9013 (1.2); 7.3775 (1.8); 7.3555 (1.9); 7.3209 (1.2); 7.3170 (1.2); 7.3015 (1.4); 7.2976 (1.4); 7.2600 (32.7); 6.9364 (1.3); 6.9241 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9176 (1.2); 7.9136 (1.3); 7.9053 (1.3); 7.9013 (1.2); 7.3775 (1.8); 7.3555 (1.9); 7.3209 (1.2); 7.3170 (1.2); 7.3015 (1.4); 7.2976 (1.4); 7,2600 (32.7); 6.9364 (1.3); 6.9241
(1.4); 6.9182 (2.1); 6.9046 (1.4); 6.9022 (1.8); 6.2930 (3.0); 5.0193 (0.9); 4.9794 (2.7); 4.9453 (2.7);(1.4); 6.9182 (2.1); 6.9046 (1.4); 6.9022 (1.8); 6.2930 (3.0); 5.0193 (0.9); 4,9794 (2.7); 4.9453 (2.7);
4.9055 (0.9); 4.2753 (1.0); 4.2665 (1.5); 4.2530 (1.0); 3.6895 (1.8); 3.6773 (2.0); 3.6653 (1.6); 3.61144.9055 (0.9); 4.2753 (1.0); 4.2665 (1.5); 4.2530 (1.0); 3.6895 (1.8); 3.6773 (2.0); 3.6653 (1.6); 3.6114
(1.2); 3.6007 (1.7); 3.5957 (1.6); 3.5890 (2.5); 3.5255 (2.5); 3.5188 (1.7); 3.5062 (4.7); 3.5034 (5.4);(1.2); 3.6007 (1.7); 3.5957 (1.6); 3.5890 (2.5); 3.5255 (2.5); 3.5188 (1.7); 3,5062 (4.7); 3,5034 (5.4);
3.3722 (16.0); 1.5413 (11.6); 0.8822 (0.6); 0.0080 (1.8); -0.0002 (42.1); -0.0085 (1.8) 3.3722 (16.0); 1.5413 (11.6); 0.8822 (0.6); 0.0080 (1.8); -0.0002 (42.1); -0.0085 (1.8)
Beispiel Nr. 1.15-26: Example no.1.15-26:
1H-NMR(400.0 MHz, CDC13): 5= 7.9215 (1.2); 7.9176 (1.4); 7.9092 (1.4); 7.9053 (1.2); 7.3787 (1.8); 7.3565 (1.8); 7.3288 (1.2); 7.3248 (1.3); 7.3094 (1.5); 7.3054 (1.4); 7.2605 (23.1); 6.9403 (1.4); 6.9276 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9215 (1.2); 7.9176 (1.4); 7.9092 (1.4); 7.9053 (1.2); 7.3787 (1.8); 7.3565 (1.8); 7.3288 (1.2); 7.3248 (1.3); 7.3094 (1.5); 7.3054 (1.4); 7.2605 (23.1); 6.9403 (1.4); 6.9276
(2.6); 6.9209 (1.4); 6.9105 (1.9); 6.2996 (3.1); 4.9825 (0.9); 4.9428 (2.9); 4.9133 (2.8); 4.8736 (0.9); 4.2066 (0.8); 4.1991 (0.8); 4.1905 (1.5); 4.1831 (1.5); 4.1741 (0.9); 4.1669 (0.8); 3.5076 (4.5); 3.5047(2.6); 6.9209 (1.4); 6.9105 (1.9); 6.2996 (3.1); 4.9825 (0.9); 4.9428 (2.9); 4.9133 (2.8); 4.8736 (0.9); 4.2066 (0.8); 4.1991 (0.8); 4.1905 (1.5); 4.1831 (1.5); 4.1741 (0.9); 4.1669 (0.8); 3,5076 (4.5); 3,5047
(4.7); 3.3808 (1.7); 3.3652 (3.7); 3.3496 (1.8); 3.2912 (16.0); 2.6149 (2.5); 2.0451 (0.5); 1.8839 (1.6); 1.8679 (2.4); 1.8520 (1.6); 1.5463 (15.7); 1.2595 (0.8); 0.8821 (1.0); 0.0080 (1.2); -0.0002 (29.4); - 0.0084 (1.5) (4.7); 3.3808 (1.7); 3.3652 (3.7); 3.3496 (1.8); 3.2912 (16.0); 2.6149 (2.5); 2.0451 (0.5); 1.8839 (1.6); 1.8679 (2.4); 1.8520 (1.6); 1.5463 (15.7); 1.2595 (0.8); 0.8821 (1.0); 0.0080 (1.2); -0.0002 (29.4); - 0.0084 (1.5)
Beispiel Nr. 1.15-31 : Example no.1.15-31:
1H-NMR(400.0 MHz, CDC13): 5= 7.9224 (1.1); 7.9184 (1.2); 7.9100 (1.2); 7.9060 (1.2); 7.3842 (1.6); 7.3621 (1.6); 7.3219 (1.1); 7.3179 (1.1); 7.3025 (1.3); 7.2985 (1.2); 7.2604 (18.4); 6.9442 (1.3); 6.9319 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9224 (1.1); 7.9184 (1.2); 7.9100 (1.2); 7.9060 (1.2); 7.3842 (1.6); 7.3621 (1.6); 7.3219 (1.1); 7.3179 (1.1); 7.3025 (1.3); 7.2985 (1.2); 7.2604 (18.4); 6.9442 (1.3); 6.9319
(1.2); 6.9248 (1.2); 6.9125 (1.2); 6.9030 (1.5); 6.8867 (1.5); 6.2985 (2.6); 5.3000 (3.8); 4.9964 (0.9);(1.2); 6.9248 (1.2); 6.9125 (1.2); 6.9030 (1.5); 6.8867 (1.5); 6.2985 (2.6); 5,3000 (3.8); 4.9964 (0.9);
4.9567 (2.6); 4.9237 (2.6); 4.8840 (0.9); 4.2939 (0.7); 4.2857 (0.8); 4.2769 (1.3); 4.2677 (1.1); 4.25884.9567 (2.6); 4.9237 (2.6); 4.8840 (0.9); 4.2939 (0.7); 4.2857 (0.8); 4.2769 (1.3); 4.2677 (1.1); 4.2588
(0.8); 4.2508 (0.7); 3.5130 (3.6); 3.5100 (3.7); 2.7105 (1.9); 2.6929 (2.3); 2.6756 (1.7); 2.1718 (1.7);(0.8); 4.2508 (0.7); 3.5130 (3.6); 3.5100 (3.7); 2.7105 (1.9); 2.6929 (2.3); 2.6756 (1.7); 2.1718 (1.7);
2.1221 (16.0); 1.5411 (5.2); 0.0080 (0.7); -0.0002 (26.6); -0.0085 (0.7) Beispiel Nr. 1.15-41: 2.1221 (16.0); 1.5411 (5.2); 0.0080 (0.7); -0.0002 (26.6); -0.0085 (0.7) Example no.1.15-41:
1H-NMR(400.0 MHz, CDC13): d= 7.9150 (2.3); 7.9111 (2.5); 7.9027 (2.6); 7.8987 (2.5); 7.3888 (3.4); 7.3669 (3.4); 7.3301 (2.4); 7.3262 (2.5); 7.3107 (2.8); 7.3067 (2.6); 7.2601 (56.7); 7.2561 (1.0); 7.2553 (0.9); 6.9502 (2.8); 6.9379 (2.7); 6.9308 (2.6); 6.9184 (2.6); 6.8452 (3.2); 6.8290 (3.3); 6.2886 (5.6); 5.0254 (2.2); 4.9855 (5.4); 4.9409 (5.4); 4.9010 (2.2); 4.3622 (0.8); 4.3505 (2.4); 4.3384 (2.5); 4.3270 (0.9); 4.1224 (3.9); 4.1107 (6.3); 4.0989 (3.0); 3.5073 (7.7); 3.5043 (7.9); 1.5377 (16.0); 1.2628 (0.6); 0.8820 (1.1); 0.0079 (2.1); 0.0054 (0.5); 0.0046 (0.6); -0.0002 (79.4); -0.0027 (3.6); -0.0044 (1.5); - 0.0052 (1.2); -0.0061 (1.0); -0.0069 (1.0); -0.0085 (2.5) 1 H-NMR (400.0 MHz, CDC1 3): d = 7.9150 (2.3); 7.9111 (2.5); 7.9027 (2.6); 7.8987 (2.5); 7.3888 (3.4); 7.3669 (3.4); 7.3301 (2.4); 7.3262 (2.5); 7.3107 (2.8); 7.3067 (2.6); 7.2601 (56.7); 7.2561 (1.0); 7.2553 (0.9); 6.9502 (2.8); 6.9379 (2.7); 6.9308 (2.6); 6.9184 (2.6); 6.8452 (3.2); 6.8290 (3.3); 6.2886 (5.6); 5.0254 (2.2); 4.9855 (5.4); 4,9409 (5.4); 4.9010 (2.2); 4.3622 (0.8); 4.3505 (2.4); 4.3384 (2.5); 4.3270 (0.9); 4.1224 (3.9); 4.1107 (6.3); 4.0989 (3.0); 3,5073 (7.7); 3,5043 (7.9); 1.5377 (16.0); 1.2628 (0.6); 0.8820 (1.1); 0.0079 (2.1); 0.0054 (0.5); 0.0046 (0.6); -0.0002 (79.4); -0.0027 (3.6); -0.0044 (1.5); - 0.0052 (1.2); -0.0061 (1.0); -0.0069 (1.0); -0.0085 (2.5)
Beispiel Nr. 1.15-72: Example no.1.15-72:
1H-NMR(400.0 MHz, CDC13): d= 7.9148 (1.2); 7.9109 (1.3); 7.9024 (1.3); 7.8986 (1.3); 7.3861 (1.8); 7.3641 (1.9); 7.3114 (1.0); 7.2932 (1.1); 7.2605 (19.8); 6.9428 (1.3); 6.9305 (1.4); 6.9234 (1.3); 6.9110 (1.3); 6.9066 (1.9); 6.8900 (1.8); 6.3145 (1.8); 6.2923 (1.8); 4.9908 (0.6); 4.9511 (1.7); 4.9474 (1.7); 4.9106 (1.7); 4.9075 (1.8); 4.8678 (0.6); 4.1307 (0.8); 4.1128 (1.1); 4.0947 (0.8); 4.0783 (0.6); 4.0492 (0.7); 4.0290 (0.7); 4.0150 (0.6); 3.9946 (0.6); 3.8131 (0.8); 3.7993 (0.9); 3.7926 (0.6); 3.7786 (0.6); 3.7352 (1.3); 3.7167 (1.5); 3.6981 (0.9); 3.5086 (5.9); 3.4945 (1.1); 3.4801 (0.6); 3.4724 (0.8); 3.4581 (0.5); 2.6148 (2.1); 2.5470 (0.5); 2.0450 (2.6); 1.5476 (16.0); 1.2771 (1.6); 1.2595 (3.1); 1.2417 (1.0); 0.8988 (1.2); 0.8820 (3.5); 0.8645 (1.5); -0.0002 (24.9); -0.0085 (1.2) 1 H-NMR (400.0 MHz, CDCl 3 ): d = 7.9148 (1.2); 7.9109 (1.3); 7.9024 (1.3); 7.8986 (1.3); 7.3861 (1.8); 7.3641 (1.9); 7.3114 (1.0); 7.2932 (1.1); 7.2605 (19.8); 6.9428 (1.3); 6.9305 (1.4); 6.9234 (1.3); 6.9110 (1.3); 6.9066 (1.9); 6.8900 (1.8); 6.3145 (1.8); 6.2923 (1.8); 4,9908 (0.6); 4.9511 (1.7); 4,9474 (1.7); 4.9106 (1.7); 4.9075 (1.8); 4.8678 (0.6); 4.1307 (0.8); 4.1128 (1.1); 4.0947 (0.8); 4.0783 (0.6); 4.0492 (0.7); 4.0290 (0.7); 4.0150 (0.6); 3.9946 (0.6); 3.8131 (0.8); 3.7993 (0.9); 3.7926 (0.6); 3.7786 (0.6); 3.7352 (1.3); 3.7167 (1.5); 3.6981 (0.9); 3,5086 (5.9); 3.4945 (1.1); 3.4801 (0.6); 3.4724 (0.8); 3.4581 (0.5); 2.6148 (2.1); 2.5470 (0.5); 2.0450 (2.6); 1.5476 (16.0); 1.2771 (1.6); 1.2595 (3.1); 1.2417 (1.0); 0.8988 (1.2); 0.8820 (3.5); 0.8645 (1.5); -0.0002 (9/24); -0.0085 (1.2)
Beispiel Nr. 1.15-115: Example no.1.15-115:
1H-NMR(400.0 MHz, CDC13): d= 7.9152 (1.8); 7.9112 (1.7); 7.9029 (2.0); 7.8989 (1.8); 7.3915 (2.6); 7.3693 (2.7); 7.3214 (1.8); 7.3174 (1.8); 7.3019 (2.0); 7.2979 (1.9); 7.2599 (44.3); 6.9556 (1.8); 6.9433 (1.8); 6.9362 (1.7); 6.9238 (1.8); 6.8632 (2.5); 6.8469 (2.5); 6.2904 (4.1); 5.4784 (0.7); 5.4625 (1.4); 5.4493 (0.9); 5.0216 (1.4); 4.9817 (3.9); 4.9452 (3.9); 4.9053 (1.4); 4.8642 (1.5); 4.8450 (2.4); 4.8284 (1.6); 4.6402 (0.9); 4.6327 (1.1); 4.6199 (1.6); 4.6095 (0.9); 4.6027 (0.8); 4.1309 (1.2); 4.1130 (1.2); 3.5113 (6.4); 3.5084 (6.3); 2.0448 (5.6); 1.5398 (16.0); 1.2772 (2.2); 1.2594 (4.4); 1.2415 (1.7); 0.8990 (0.9); 0.8821 (2.8); 0.8643 (1.1); 0.0080 (2.1); -0.0002 (58.6); -0.0085 (2.4) 1 H-NMR (400.0 MHz, CDCl 3 ): d = 7.9152 (1.8); 7.9112 (1.7); 7.9029 (2.0); 7.8989 (1.8); 7.3915 (2.6); 7.3693 (2.7); 7.3214 (1.8); 7.3174 (1.8); 7.3019 (2.0); 7.2979 (1.9); 7.2599 (44.3); 6.9556 (1.8); 6.9433 (1.8); 6.9362 (1.7); 6.9238 (1.8); 6.8632 (2.5); 6.8469 (2.5); 6.2904 (4.1); 5.4784 (0.7); 5.4625 (1.4); 5.4493 (0.9); 5.0216 (1.4); 4.9817 (3.9); 4.9452 (3.9); 4.9053 (1.4); 4.8642 (1.5); 4.8450 (2.4); 4.8284 (1.6); 4.6402 (0.9); 4.6327 (1.1); 4.6199 (1.6); 4.6095 (0.9); 4.6027 (0.8); 4.1309 (1.2); 4.1130 (1.2); 3.5113 (6.4); 3,5084 (6.3); 2.0448 (5.6); 1.5398 (16.0); 1.2772 (2.2); 1.2594 (4.4); 1.2415 (1.7); 0.8990 (0.9); 0.8821 (2.8); 0.8643 (1.1); 0.0080 (2.1); -0.0002 (58.6); -0.0085 (2.4)
Beispiel Nr. 1.15-154: Example no.1.15-154:
1H-NMR(400.0 MHz, CDC13): d= 7.9187 (1.1); 7.9147 (1.2); 7.9064 (1.2); 7.9024 (1.1); 7.3787 (1.6); 7.3567 (1.6); 7.3205 (1.1); 7.3165 (1.1); 7.3011 (1.2); 7.2971 (1.2); 7.2617 (13.9); 6.9375 (1.3); 6.9252 (1.3); 6.9192 (1.9); 6.9057 (1.4); 6.9033 (1.6); 6.2936 (2.8); 5.0159 (0.8); 4.9762 (2.5); 4.9453 (2.5); 4.9056 (0.8); 4.2647 (1.0); 4.2552 (1.0); 4.2533 (1.1); 4.2493 (0.9); 4.2404 (1.1); 3.6882 (1.5); 3.6810 1 H-NMR (400.0 MHz, CDC1 3): d = 7.9187 (1.1); 7.9147 (1.2); 7.9064 (1.2); 7.9024 (1.1); 7.3787 (1.6); 7.3567 (1.6); 7.3205 (1.1); 7.3165 (1.1); 7.3011 (1.2); 7.2971 (1.2); 7.2617 (13.9); 6.9375 (1.3); 6.9252 (1.3); 6.9192 (1.9); 6.9057 (1.4); 6.9033 (1.6); 6.2936 (2.8); 5.0159 (0.8); 4.9762 (2.5); 4,9453 (2.5); 4.9056 (0.8); 4.2647 (1.0); 4.2552 (1.0); 4.2533 (1.1); 4.2493 (0.9); 4.2404 (1.1); 3.6882 (1.5); 3.6810
(0.6); 3.6783 (1.1); 3.6760 (1.6); 3.6640 (1.5); 3.6551 (16.0); 3.6487 (0.6); 3.6447 (1.6); 3.6427 (1.7);(0.6); 3.6783 (1.1); 3.6760 (1.6); 3.6640 (1.5); 3.6551 (16.0); 3.6487 (0.6); 3.6447 (1.6); 3.6427 (1.7);
3.6373 (1.4); 3.6302 (2.6); 3.6193 (7.0); 3.6166 (2.9); 3.6097 (0.6); 3.5573 (2.2); 3.5501 (1.3); 3.54533.6373 (1.4); 3.6302 (2.6); 3.6193 (7.0); 3.6166 (2.9); 3.6097 (0.6); 3.5573 (2.2); 3.5501 (1.3); 3.5453
(1.5); 3.5427 (1.3); 3.5345 (1.1); 3.5070 (3.7); 3.5041 (3.7); 3.3750 (15.9); 1.5863 (2.5); -0.0002 (15.2) Beispiel Nr. 1.15-166: (1.5); 3.5427 (1.3); 3.5345 (1.1); 3,5070 (3.7); 3,5041 (3.7); 3.3750 (15.9); 1.5863 (2.5); -0.0002 (15.2) Example no.1.15-166:
1H-NMR(400.0 MHz, CDC13): 5= 7.9136 (2.0); 7.9097 (2.2); 7.9013 (2.3); 7.8973 (2.2); 7.3992 (3.0); 7.3773 (3.0); 7.3403 (2.0); 7.3364 (2.2); 7.3209 (2.4); 7.3169 (2.3); 7.2603 (64.0); 6.9791 (2.5); 6.9668 (2.4); 6.9597 (2.2); 6.9473 (2.2); 6.8460 (2.8); 6.8298 (2.9); 6.3297 (5.0); 5.3001 (16.0); 5.0149 (2.1); 4.9751 (4.7); 4.9210 (4.6); 4.8811 (2.1); 4.6101 (0.7); 4.5937 (1.2); 4.5792 (1.8); 4.5686 (1.2); 4.5654 (1.2); 4.5544 (1.9); 4.5399 (1.2); 4.5237 (0.7); 3.5179 (6.7); 3.5149 (7.0); 3.3072 (1.5); 3.2938 (2.9); 3.2799 (1.4); 2.9219 (14.0); 2.1719 (4.2); 1.5391 (15.6); 0.0079 (2.4); 0.0055 (0.7); -0.0002 (86.7); - 0.0068 (1.0); -0.0085 (2.8) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9136 (2.0); 7.9097 (2.2); 7.9013 (2.3); 7,8973 (2.2); 7,3992 (3.0); 7.3773 (3.0); 7.3403 (2.0); 7.3364 (2.2); 7.3209 (2.4); 7.3169 (2.3); 7.2603 (64.0); 6.9791 (2.5); 6.9668 (2.4); 6.9597 (2.2); 6.9473 (2.2); 6.8460 (2.8); 6.8298 (2.9); 6.3297 (5.0); 5,3001 (16.0); 5.0149 (2.1); 4,9751 (4.7); 4.9210 (4.6); 4.8811 (2.1); 4.6101 (0.7); 4.5937 (1.2); 4.5792 (1.8); 4.5686 (1.2); 4.5654 (1.2); 4.5544 (1.9); 4.5399 (1.2); 4.5237 (0.7); 3.5179 (6.7); 3.5149 (7.0); 3.3072 (1.5); 3.2938 (2.9); 3.2799 (1.4); 2.9219 (14.0); 2.1719 (4.2); 1.5391 (15.6); 0.0079 (2.4); 0.0055 (0.7); -0.0002 (86.7); - 0.0068 (1.0); -0.0085 (2.8)
Beispiel Nr. 1.15-176: Example no.1.15-176:
1H-NMR(400.0 MHz, CDC13): 5= 7.9361 (2.0); 7.9321 (2.1); 7.9238 (2.2); 7.9198 (2.2); 7.5193 (0.6); 7.3994 (3.3); 7.3774 (3.3); 7.3695 (2.1); 7.3655 (2.2); 7.3500 (2.4); 7.3460 (2.3); 7.2604 (104.1); 6.9964 (0.6); 6.9875 (2.4); 6.9752 (2.3); 6.9680 (2.2); 6.9557 (2.1); 6.8072 (3.1); 6.7909 (3.1); 6.3085 (5.4); 5.2999 (5.2); 5.0404 (1.6); 5.0002 (5.7); 4.9740 (5.6); 4.9338 (1.6); 4.7514 (16.0); 3.5163 (7.6); 3.5134 (7.8); 2.0074 (7.0); 1.5403 (7.8); 1.2536 (0.6); 0.0080 (2.1); -0.0002 (62.9); -0.0084 (1.8) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9361 (2.0); 7.9321 (2.1); 7.9238 (2.2); 7.9198 (2.2); 7.5193 (0.6); 7,3994 (3.3); 7.3774 (3.3); 7.3695 (2.1); 7.3655 (2.2); 7,3500 (2.4); 7.3460 (2.3); 7.2604 (104.1); 6.9964 (0.6); 6.9875 (2.4); 6.9752 (2.3); 6.9680 (2.2); 6.9557 (2.1); 6.8072 (3.1); 6.7909 (3.1); 6.3085 (5.4); 5,2999 (5.2); 5.0404 (1.6); 5,0002 (5.7); 4.9740 (5.6); 4,9338 (1.6); 4.7514 (16.0); 3.5163 (7.6); 3.5134 (7.8); 2.0074 (7.0); 1.5403 (7.8); 1.2536 (0.6); 0.0080 (2.1); -0.0002 (62.9); -0.0084 (1.8)
Beispiel Nr. 1.15-201 : Example no.1.15-201:
1H-NMR(400.0 MHz, CDC13): 5= 7.8749 (2.8); 7.8709 (3.1); 7.8626 (3.1); 7.8586 (3.1); 7.3501 (4.1); 7.3279 (4.2); 7.2690 (2.9); 7.2650 (3.0); 7.2495 (3.4); 7.2456 (3.2); 7.2308 (52.3); 6.9191 (3.9); 6.9028 (4.0); 6.8941 (3.4); 6.8818 (3.3); 6.8747 (3.1); 6.8624 (3.1); 6.2636 (6.8); 4.9483 (1.2); 4.9090 (7.1); 4.8955 (7.1); 4.8562 (1.3); 3.8108 (0.5); 3.7757 (8.2); 3.7715 (8.2); 3.7364 (0.5); 3.4811 (9.2); 3.4781 (9.6); 1.9781 (8.2); 1.5108 (16.0); 0.0081 (3.4); -0.0002 (120.4); -0.0087 (3.4); -0.0215 (2.1); -0.0240 (0.6); -0.0248 (0.6); -0.0296 (71.6); -0.0354 (0.8); -0.0363 (0.7); -0.0379 (2.0) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.8749 (2.8); 7.8709 (3.1); 7.8626 (3.1); 7.8586 (3.1); 7.3501 (4.1); 7.3279 (4.2); 7.2690 (2.9); 7.2650 (3.0); 7.2495 (3.4); 7.2456 (3.2); 7.2308 (52.3); 6.9191 (3.9); 6.9028 (4.0); 6.8941 (3.4); 6.8818 (3.3); 6.8747 (3.1); 6.8624 (3.1); 6.2636 (6.8); 4,9483 (1.2); 4.9090 (7.1); 4.8955 (7.1); 4.8562 (1.3); 3.8108 (0.5); 3.7757 (8.2); 3.7715 (8.2); 3.7364 (0.5); 3.4811 (9.2); 3.4781 (9.6); 1.9781 (8.2); 1.5108 (16.0); 0.0081 (3.4); -0.0002 (120.4); -0.0087 (3.4); -0.0215 (2.1); -0.0240 (0.6); -0.0248 (0.6); -0.0296 (71.6); -0.0354 (0.8); -0.0363 (0.7); -0.0379 (2.0)
Beispiel Nr. 1.15-286: Example no.1.15-286:
1H-NMR(400.0 MHz, CDC13): 5= 8.5414 (1.5); 8.5293 (1.5); 7.9055 (2.6); 7.9015 (2.8); 7.8931 (2.8); 7.8891 (2.8); 7.6904 (1.2); 7.6860 (1.2); 7.6712 (2.2); 7.6668 (2.2); 7.6519 (1.3); 7.6475 (1.3); 7.3678 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 8.5414 (1.5); 8.5293 (1.5); 7.9055 (2.6); 7.9015 (2.8); 7.8931 (2.8); 7.8891 (2.8); 7.6904 (1.2); 7.6860 (1.2); 7.6712 (2.2); 7.6668 (2.2); 7.6519 (1.3); 7.6475 (1.3); 7.3678
(4.1); 7.3457 (4.2); 7.3396 (2.8); 7.3356 (2.8); 7.3202 (3.0); 7.3161 (2.8); 7.2847 (2.2); 7.2604 (56.0);(4.1); 7.3457 (4.2); 7.3396 (2.8); 7.3356 (2.8); 7.3202 (3.0); 7.3161 (2.8); 7.2847 (2.2); 7.2604 (56.0);
7.2243 (1.1); 7.2123 (1.1); 7.2058 (1.1); 7.1935 (1.0); 6.9416 (3.0); 6.9292 (2.9); 6.9221 (2.8); 6.90987.2243 (1.1); 7.2123 (1.1); 7.2058 (1.1); 7.1935 (1.0); 6.9416 (3.0); 6.9292 (2.9); 6.9221 (2.8); 6.9098
(2.8); 6.8922 (3.9); 6.8759 (4.0); 6.2342 (7.0); 5.6484 (0.6); 5.2610 (10.3); 5.0933 (1.5); 5.0535 (6.9);(2.8); 6.8922 (3.9); 6.8759 (4.0); 6.2342 (7.0); 5.6484 (0.6); 5.2610 (10.3); 5.0933 (1.5); 5.0535 (6.9);
5.0358 (6.9); 4.9959 (1.5); 4.1487 (1.1); 4.1309 (3.4); 4.1130 (3.4); 4.0952 (1.2); 3.4802 (9.5); 3.47745.0358 (6.9); 4.9959 (1.5); 4.1487 (1.1); 4.1309 (3.4); 4.1130 (3.4); 4.0952 (1.2); 3.4802 (9.5); 3.4774
(9.7); 2.0451 (16.0); 1.5511 (12.0); 1.3031 (0.7); 1.2773 (5.4); 1.2595 (10.9); 1.2416 (4.6); 0.8989 (1.9); 0.8820 (6.7); 0.8643 (2.6); 0.0080 (1.9); -0.0002 (73.3); -0.0085 (2.1) (9.7); 2.0451 (16.0); 1.5511 (12.0); 1.3031 (0.7); 1.2773 (5.4); 1.2595 (10.9); 1.2416 (4.6); 0.8989 (1.9); 0.8820 (6.7); 0.8643 (2.6); 0.0080 (1.9); -0.0002 (73.3); -0.0085 (2.1)
Beispiel Nr. 1.15-301 : Example no.1.15-301:
1H-NMR(400.0 MHz, CDC13): 5= 9.1426 (1.6); 9.1377 (1.6); 9.1308 (1.6); 9.1260 (1.6); 7.8939 (2.5); 7.8899 (2.7); 7.8816 (2.7); 7.8776 (2.6); 7.5174 (0.8); 7.5125 (0.9); 7.4962 (3.0); 7.4913 (2.8); 7.4819 (3.5); 7.4701 (3.1); 7.4607 (0.9); 7.4489 (1.1); 7.3757 (3.5); 7.3537 (3.4); 7.3342 (2.5); 7.3302 (2.6); 7.3148 (2.9); 7.3108 (2.8); 7.2655 (0.6); 7.2646 (0.8); 7.2613 (42.1); 7.2581 (0.9); 7.2573 (0.7); 6.9537 (3.0); 6.9413 (2.9); 6.9342 (2.8); 6.9219 (2.7); 6.8236 (3.3); 6.8073 (3.3); 6.2693 (5.8); 5.5450 (0.9); 5.5109 (4.8); 5.4960 (4.6); 5.4619 (0.9); 5.3001 (16.0); 5.0952 (1.8); 5.0554 (5.9); 5.0284 (5.8); 4.9885 (1.8); 3.5065 (7.8); 3.5035 (8.0); 1.5663 (3.8); 0.0079 (1.4); 0.0046 (0.6); 0.0037 (0.8); -0.0002 (52.6); - 0.0028 (2.2); -0.0044 (0.9); -0.0053 (0.7); -0.0060 (0.6); -0.0069 (0.5); -0.0085 (1.6) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 9.1426 (1.6); 9.1377 (1.6); 9.1308 (1.6); 9.1260 (1.6); 7.8939 (2.5); 7.8899 (2.7); 7.8816 (2.7); 7.8776 (2.6); 7.5174 (0.8); 7.5125 (0.9); 7.4962 (3.0); 7.4913 (2.8); 7.4819 (3.5); 7.4701 (3.1); 7.4607 (0.9); 7.4489 (1.1); 7,3757 (3.5); 7.3537 (3.4); 7.3342 (2.5); 7.3302 (2.6); 7.3148 (2.9); 7.3108 (2.8); 7.2655 (0.6); 7.2646 (0.8); 7.2613 (42.1); 7.2581 (0.9); 7.2573 (0.7); 6.9537 (3.0); 6.9413 (2.9); 6.9342 (2.8); 6.9219 (2.7); 6.8236 (3.3); 6.8073 (3.3); 6.2693 (5.8); 5.5450 (0.9); 5.5109 (4.8); 5,4960 (4.6); 5.4619 (0.9); 5,3001 (16.0); 5.0952 (1.8); 5.0554 (5.9); 5.0284 (5.8); 4,9885 (1.8); 3,5065 (7.8); 3,5035 (8.0); 1.5663 (3.8); 0.0079 (1.4); 0.0046 (0.6); 0.0037 (0.8); -0.0002 (52.6); - 0.0028 (2.2); -0.0044 (0.9); -0.0053 (0.7); -0.0060 (0.6); -0.0069 (0.5); -0.0085 (1.6)
Beispiel Nr. 1.15-405: Example no.1.15-405:
1H-NMR(400.0 MHz, CDC13): d= 7.9199 (1.2); 7.9159 (1.3); 7.9075 (1.3); 7.9036 (1.3); 7.3857 (1.9); 7.3637 (1.9); 7.3232 (1.2); 7.3192 (1.3); 7.3037 (1.4); 7.2998 (1.4); 7.2607 (28.3); 6.9457 (1.4); 6.9334 1 H-NMR (400.0 MHz, CDCl 3 ): d = 7.9199 (1.2); 7.9159 (1.3); 7.9075 (1.3); 7.9036 (1.3); 7,3857 (1.9); 7.3637 (1.9); 7,3232 (1.2); 7.3192 (1.3); 7.3037 (1.4); 7.2998 (1.4); 7.2607 (28.3); 6.9457 (1.4); 6.9334
(1.4); 6.9263 (1.3); 6.9140 (1.3); 6.8899 (1.7); 6.8736 (1.7); 6.3012 (3.1); 5.3001 (2.7); 5.0213 (1.1);(1.4); 6.9263 (1.3); 6.9140 (1.3); 6.8899 (1.7); 6.8736 (1.7); 6.3012 (3.1); 5,3001 (2.7); 5.0213 (1.1);
4.9814 (2.9); 4.9422 (2.9); 4.9024 (1.1); 4.3201 (0.6); 4.3123 (0.7); 4.3084 (1.2); 4.3012 (1.1); 4.29944.9814 (2.9); 4.9422 (2.9); 4.9024 (1.1); 4,3201 (0.6); 4.3123 (0.7); 4.3084 (1.2); 4.3012 (1.1); 4.2994
(1.3); 4.2932 (1.1); 4.2904 (1.2); 4.2474 (1.2); 4.2445 (1.4); 4.2409 (0.5); 4.2323 (1.6); 4.2225 (0.7);(1.3); 4.2932 (1.1); 4.2904 (1.2); 4.2474 (1.2); 4.2445 (1.4); 4.2409 (0.5); 4.2323 (1.6); 4.2225 (0.7);
4.2206 (0.7); 3.5112 (4.1); 3.5083 (4.3); 2.1720 (2.0); 2.0313 (16.0); 1.5481 (13.3); 0.0079 (1.0); - 0.0002 (33.4); -0.0085 (0.9) 4.2206 (0.7); 3.5112 (4.1); 3,5083 (4.3); 2.1720 (2.0); 2.0313 (16.0); 1.5481 (13.3); 0.0079 (1.0); - 0.0002 (33.4); -0.0085 (0.9)
Beispiel Nr. 1.15-422: Example no.1.15-422:
1H-NMR(400.0 MHz, CDC13): d= 7.9188 (2.6); 7.9148 (2.8); 7.9065 (2.8); 7.9025 (2.8); 7.3773 (4.2); 7.3552 (4.2); 7.3374 (2.7); 7.3335 (2.7); 7.3180 (3.1); 7.3140 (2.9); 7.2606 (35.3); 6.9440 (3.0); 6.9316 (2.9); 6.9245 (2.8); 6.9100 (4.4); 6.8935 (4.0); 6.2922 (7.2); 5.0229 (1.7); 4.9830 (6.8); 4.9609 (6.7); 4.9209 (1.7); 4.6318 (2.0); 4.6181 (4.5); 4.6046 (2.2); 4.1122 (3.9); 4.1051 (4.0); 4.0989 (3.9); 4.0913 1 H-NMR (400.0 MHz, CDC1 3): d = 7.9188 (2.6); 7.9148 (2.8); 7.9065 (2.8); 7.9025 (2.8); 7.3773 (4.2); 7.3552 (4.2); 7.3374 (2.7); 7.3335 (2.7); 7.3180 (3.1); 7.3140 (2.9); 7.2606 (35.3); 6.9440 (3.0); 6.9316 (2.9); 6.9245 (2.8); 6.9100 (4.4); 6.8935 (4.0); 6.2922 (7.2); 5.0229 (1.7); 4.9830 (6.8); 4,9609 (6.7); 4,9209 (1.7); 4.6318 (2.0); 4.6181 (4.5); 4.6046 (2.2); 4.1122 (3.9); 4.1051 (4.0); 4.0989 (3.9); 4.0913
(3.6); 4.0767 (0.6); 3.6973 (0.5); 3.6847 (0.6); 3.6797 (1.6); 3.6738 (0.7); 3.6671 (1.6); 3.6618 (2.2); 3.6561 (2.2); 3.6494 (1.7); 3.6437 (2.6); 3.6385 (2.3); 3.6319 (0.6); 3.6259 (2.2); 3.6208 (0.8); 3.6083 (0.7); 3.5556 (0.7); 3.5496 (0.7); 3.5379 (2.1); 3.5320 (2.7); 3.5261 (0.7); 3.5202 (2.4); 3.5142 (4.4); 3.5072 (10.8); 3.5042 (10.8); 3.4968 (2.9); 3.4908 (1.8); 3.4791 (0.6); 3.4732 (0.5); 1.5462 (12.7); 1.2545 (1.0); 1.2368 (1.4); 1.2191 (0.7); 1.1998 (7.6); 1.1920 (7.8); 1.1822 (16.0); 1.1744 (15.8); 1.1645(3.6); 4.0767 (0.6); 3.6973 (0.5); 3.6847 (0.6); 3.6797 (1.6); 3.6738 (0.7); 3.6671 (1.6); 3.6618 (2.2); 3.6561 (2.2); 3.6494 (1.7); 3.6437 (2.6); 3.6385 (2.3); 3.6319 (0.6); 3.6259 (2.2); 3.6208 (0.8); 3.6083 (0.7); 3.5556 (0.7); 3.5496 (0.7); 3.5379 (2.1); 3.5320 (2.7); 3.5261 (0.7); 3.5202 (2.4); 3.5142 (4.4); 3,5072 (10.8); 3,5042 (10.8); 3.4968 (2.9); 3.4908 (1.8); 3.4791 (0.6); 3.4732 (0.5); 1.5462 (12.7); 1.2545 (1.0); 1.2368 (1.4); 1.2191 (0.7); 1.1998 (7.6); 1.1920 (7.8); 1.1822 (16.0); 1.1744 (15.8); 1.1645
(7.7); 1.1567 (7.5); 0.0079 (1.3); -0.0002 (49.0); -0.0085 (1.5) (7.7); 1.1567 (7.5); 0.0079 (1.3); -0.0002 (49.0); -0.0085 (1.5)
Beispiel Nr. 1.15-424: Example no.1.15-424:
1H-NMR(400.0 MHz, CDC13): d= 7.9299 (4.0); 7.9259 (4.2); 7.9176 (4.3); 7.9136 (4.2); 7.3754 (6.4); 7.3533 (6.6); 7.3462 (4.2); 7.3422 (4.1); 7.3267 (4.6); 7.3228 (4.5); 7.2603 (58.8); 6.9472 (4.7); 6.9348 (4.5); 6.9278 (4.3); 6.9154 (4.2); 6.9092 (6.2); 6.8929 (6.2); 6.2952 (11.0); 5.2998 (0.6); 5.0871 (3.5); 5.0778 (7.9); 5.0685 (3.8); 5.0365 (2.9); 4.9965 (10.4); 4.9707 (10.4); 4.9307 (2.9); 4.1579 (7.2); 4.1549 (7.3); 4.1488 (7.2); 4.1455 (6.8); 4.1162 (0.5); 3.9596 (1.5); 3.9428 (4.6); 3.9393 (4.1); 3.9350 (4.4); 3.9300 (4.4); 3.9267 (1.9); 3.9237 (4.7); 3.9135 (1.7); 3.9100 (2.0); 3.9049 (2.1); 3.9012 (1.6); 3.8900 (3.8); 3.8851 (4.1); 3.8800 (4.3); 3.8754 (4.0); 3.8723 (4.3); 3.8704 (4.3); 3.8564 (1.4); 3.5045 (15.0); 3.5016 (15.3); 1.5428 (16.0); 1.2640 (2.8); 0.8990 (1.4); 0.8820 (4.7); 0.8642 (1.9); 0.0693 (0.6); 0.0080 (2.1); -0.0002 (77.5); -0.0085 (2.4) 1 H-NMR (400.0 MHz, CDCl 3 ): d = 7.9299 (4.0); 7.9259 (4.2); 7.9176 (4.3); 7.9136 (4.2); 7.3754 (6.4); 7.3533 (6.6); 7.3462 (4.2); 7.3422 (4.1); 7.3267 (4.6); 7.3228 (4.5); 7.2603 (58.8); 6.9472 (4.7); 6.9348 (4.5); 6.9278 (4.3); 6.9154 (4.2); 6.9092 (6.2); 6.8929 (6.2); 6.2952 (11.0); 5,2998 (0.6); 5.0871 (3.5); 5.0778 (7.9); 5.0685 (3.8); 5.0365 (2.9); 4.9965 (10.4); 4,9707 (10.4); 4.9307 (2.9); 4.1579 (7.2); 4.1549 (7.3); 4.1488 (7.2); 4.1455 (6.8); 4.1162 (0.5); 3.9596 (1.5); 3.9428 (4.6); 3.9393 (4.1); 3.9350 (4.4); 3.9300 (4.4); 3.9267 (1.9); 3.9237 (4.7); 3.9135 (1.7); 3,9100 (2.0); 3.9049 (2.1); 3.9012 (1.6); 3.8900 (3.8); 3.8851 (4.1); 3.8800 (4.3); 3.8754 (4.0); 3.8723 (4.3); 3.8704 (4.3); 3.8564 (1.4); 3,5045 (15.0); 3,5016 (15.3); 1.5428 (16.0); 1.2640 (2.8); 0.8990 (1.4); 0.8820 (4.7); 0.8642 (1.9); 0.0693 (0.6); 0.0080 (2.1); -0.0002 (77.5); -0.0085 (2.4)
Beispiel Nr. 1.16-422 Example No. 1.16-422
1H-NMR(400.0 MHz, CDC13): 5= 7.9223 (1.2); 7.9183 (1.3); 7.9100 (1.3); 7.9060 (1.2); 7.5398 (1.8); 7.5184 (1.8); 7.3462 (1.2); 7.3422 (1.2); 7.3268 (1.4); 7.3228 (1.3); 7.2618 (9.6); 6.9456 (1.5); 6.9333 (1.4); 6.9262 (1.2); 6.9138 (1.2); 6.8774 (2.0); 6.8612 (1.9); 6.2889 (3.9); 5.0223 (0.8); 4.9823 (2.8); 4.9778 (1.0); 4.9589 (2.8); 4.9478 (0.9); 4.9190 (0.8); 4.6311 (0.8); 4.6174 (1.9); 4.6084 (0.7); 4.6040 (0.9); 4.1127 (0.6); 4.1097 (1.6); 4.1020 (1.6); 4.0963 (2.1); 4.0881 (1.7); 4.0827 (0.6); 4.0727 (0.6); 3.6794 (0.8); 3.6665 (0.7); 3.6617 (1.0); 3.6559 (1.1); 3.6488 (0.8); 3.6431 (1.2); 3.6383 (1.2); 3.6254 (1.0); 3.5379 (1.0); 3.5319 (1.2); 3.5203 (1.1); 3.5143 (1.8); 3.5122 (1.0); 3.5043 (5.4); 3.5016 (5.6); 3.4908 (0.8); 2.1718 (2.0); 2.0454 (1.7); 1.5713 (16.0); 1.2773 (1.0); 1.2645 (1.7); 1.2596 (2.0); 1.2546 (1.0); 1.2417 (0.7); 1.2369 (0.9); 1.1999 (4.3); 1.1918 (3.9); 1.1823 (8.9); 1.1742 (7.8); 1.1646 (4.2); 1.1566 (3.7); 0.8989 (0.9); 0.8820 (3.4); 0.8643 (1.2); -0.0002 (8.6) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.9223 (1.2); 7.9183 (1.3); 7.9100 (1.3); 7.9060 (1.2); 7.5398 (1.8); 7.5184 (1.8); 7,3462 (1.2); 7.3422 (1.2); 7.3268 (1.4); 7.3228 (1.3); 7.2618 (9.6); 6.9456 (1.5); 6.9333 (1.4); 6.9262 (1.2); 6.9138 (1.2); 6.8774 (2.0); 6.8612 (1.9); 6.2889 (3.9); 5.0223 (0.8); 4.9823 (2.8); 4,9778 (1.0); 4.9589 (2.8); 4.9478 (0.9); 4.9190 (0.8); 4.6311 (0.8); 4.6174 (1.9); 4.6084 (0.7); 4.6040 (0.9); 4.1127 (0.6); 4,1097 (1.6); 4.1020 (1.6); 4.0963 (2.1); 4.0881 (1.7); 4.0827 (0.6); 4.0727 (0.6); 3.6794 (0.8); 3.6665 (0.7); 3.6617 (1.0); 3.6559 (1.1); 3.6488 (0.8); 3.6431 (1.2); 3.6383 (1.2); 3.6254 (1.0); 3.5379 (1.0); 3.5319 (1.2); 3.5203 (1.1); 3.5143 (1.8); 3.5122 (1.0); 3,5043 (5.4); 3,5016 (5.6); 3.4908 (0.8); 2.1718 (2.0); 2.0454 (1.7); 1.5713 (16.0); 1.2773 (1.0); 1.2645 (1.7); 1.2596 (2.0); 1.2546 (1.0); 1.2417 (0.7); 1.2369 (0.9); 1.1999 (4.3); 1.1918 (3.9); 1.1823 (8.9); 1.1742 (7.8); 1.1646 (4.2); 1.1566 (3.7); 0.8989 (0.9); 0.8820 (3.4); 0.8643 (1.2); -0.0002 (8.6)
Beispiel Nr. 1.31-23 Example No. 1.31-23
1H-NMR(400.0 MHz, CDC13): 5= 7.8484 (5.9); 7.8438 (6.0); 7.4184 (4.6); 7.4100 (5.4); 7.4062 (5.2); 7.3951 (4.7); 7.2604 (33.9); 7.2515 (3.2); 7.2435 (3.1); 7.2389 (2.7); 6.3259 (9.4); 4.9567 (2.3); 4.9300 (7.8); 4.9096 (7.6); 4.8830 (2.3); 4.7410 (0.4); 4.3105 (0.4); 4.3025 (0.4); 4.2880 (0.4); 4.2760 (2.9); 4.2735 (3.2); 4.2688 (5.1); 4.2648 (5.1); 4.2601 (3.4); 4.2576 (3.1); 4.2453 (0.4); 3.7282 (1.8); 3.7202 (0.6); 3.7124 (0.5); 3.7007 (5.2); 3.6927 (7.5); 3.6846 (4.9); 3.6749 (0.4); 3.6696 (0.4); 3.6621 (0.5); 3.6539 (0.6); 3.6306 (4.6); 3.6233 (6.3); 3.6200 (4.6); 3.6152 (6.5); 3.5696 (0.5); 3.5596 (0.8); 3.5542 (1.0); 3.5424 (6.9); 3.5374 (5.8); 3.5299 (19.2); 3.3931 (2.5); 3.3829 (35.6); 3.3650 (0.5); 2.1637 (0.4); 1.5493 (50.0); 1.2551 (1.1); -0.0001 (46.3) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.8484 (5.9); 7.8438 (6.0); 7.4184 (4.6); 7.4100 (5.4); 7.4062 (5.2); 7,3951 (4.7); 7.2604 (33.9); 7.2515 (3.2); 7.2435 (3.1); 7.2389 (2.7); 6.3259 (9.4); 4.9567 (2.3); 4.9300 (7.8); 4.9096 (7.6); 4.8830 (2.3); 4.7410 (0.4); 4.3105 (0.4); 4.3025 (0.4); 4.2880 (0.4); 4.2760 (2.9); 4.2735 (3.2); 4.2688 (5.1); 4.2648 (5.1); 4.2601 (3.4); 4.2576 (3.1); 4.2453 (0.4); 3.7282 (1.8); 3.7202 (0.6); 3.7124 (0.5); 3.7007 (5.2); 3.6927 (7.5); 3.6846 (4.9); 3.6749 (0.4); 3.6696 (0.4); 3.6621 (0.5); 3.6539 (0.6); 3.6306 (4.6); 3.6233 (6.3); 3.6200 (4.6); 3.6152 (6.5); 3.5696 (0.5); 3.5596 (0.8); 3.5542 (1.0); 3.5424 (6.9); 3.5374 (5.8); 3.5299 (19.2); 3.3931 (2.5); 3.3829 (35.6); 3.3650 (0.5); 2.1637 (0.4); 1.5493 (50.0); 1.2551 (1.1); -0.0001 (46.3)
Beispiel Nr. 1.35-1 Example No. 1.35-1
1H-NMR(400.0 MHz, CDC13): 5= 8.0118 (1.3); 8.0077 (1.3); 7.9994 (1.3); 7.9954 (1.3); 7.5491 (1.3); 7.5450 (1.3); 7.5297 (1.4); 7.5256 (1.4); 7.5110 (2.0); 7.4901 (2.0); 7.2635 (2.2); 7.0158 (1.4); 7.0035 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 8.0118 (1.3); 8.0077 (1.3); 7.9994 (1.3); 7.9954 (1.3); 7.5491 (1.3); 7.5450 (1.3); 7.5297 (1.4); 7.5256 (1.4); 7.5110 (2.0); 7.4901 (2.0); 7.2635 (2.2); 7.0158 (1.4); 7.0035
(1.4); 6.9964 (1.4); 6.9841 (1.3); 6.9637 (1.9); 6.9492 (1.9); 6.2719 (3.6); 5.0022 (1.4); 4.9624 (2.8);(1.4); 6.9964 (1.4); 6.9841 (1.3); 6.9637 (1.9); 6.9492 (1.9); 6.2719 (3.6); 5.0022 (1.4); 4.9624 (2.8);
4.8951 (2.8); 4.8552 (1.4); 4.2026 (0.9); 4.1916 (2.5); 4.1794 (2.5); 4.1680 (0.8); 3.5152 (2.2); 3.50344.8951 (2.8); 4.8552 (1.4); 4.2026 (0.9); 4.1916 (2.5); 4.1794 (2.5); 4.1680 (0.8); 3.5152 (2.2); 3,5034
(4.1); 3.4903 (5.8); 3.4872 (5.1); 3.2949 (16.0); 1.6014 (1.0); -0.0002 (3.2) (4.1); 3.4903 (5.8); 3.4872 (5.1); 3.2949 (16.0); 1.6014 (1.0); -0.0002 (3.2)
Beispiel Nr. 1.36-1 Example No. 1.36-1
1H-NMR(400.0 MHz, CDC13): 5= 7.7738 (2.0); 7.7672 (2.1); 7.3975 (1.9); 7.3755 (1.9); 7.2607 (9.8); 7.1175 (1.2); 7.1109 (1.1); 7.0974 (1.2); 7.0909 (1.1); 7.0004 (1.8); 6.9842 (1.8); 6.3063 (3.2); 5.0009 (0.8); 4.9609 (3.0); 4.9349 (3.0); 4.8950 (0.8); 4.2622 (1.0); 4.2591 (1.0); 4.2517 (1.4); 4.2457 (1.3); 4.2387 (1.0); 4.2357 (1.0); 3.5625 (2.0); 3.5507 (2.2); 3.5389 (1.9); 3.5202 (4.5); 3.5175 (4.7); 3.3369 (16.0); 2.0450 (1.1); 1.5511 (4.4); 1.2772 (0.5); 1.2595 (1.1); 0.8820 (1.2); -0.0002 (12.9) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.7738 (2.0); 7.7672 (2.1); 7,3975 (1.9); 7,3755 (1.9); 7.2607 (9.8); 7.1175 (1.2); 7.1109 (1.1); 7.0974 (1.2); 7.0909 (1.1); 7,0004 (1.8); 6.9842 (1.8); 6.3063 (3.2); 5,0009 (0.8); 4,9609 (3.0); 4.9349 (3.0); 4.8950 (0.8); 4.2622 (1.0); 4.2591 (1.0); 4.2517 (1.4); 4.2457 (1.3); 4.2387 (1.0); 4.2357 (1.0); 3.5625 (2.0); 3.5507 (2.2); 3.5389 (1.9); 3.5202 (4.5); 3.5175 (4.7); 3.3369 (16.0); 2.0450 (1.1); 1.5511 (4.4); 1.2772 (0.5); 1.2595 (1.1); 0.8820 (1.2); -0.0002 (12.9)
Beispiel Nr. 1.36-23 Example No. 1.36-23
1H-NMR(400.0 MHz, CDC13): 5= 7.7686 (1.5); 7.7620 (1.5); 7.3987 (1.4); 7.3767 (1.4); 7.2601 (36.0); 7.1037 (0.8); 7.0972 (0.8); 7.0835 (0.9); 7.0769 (0.8); 7.0058 (1.3); 6.9895 (1.3); 6.3117 (2.3); 4.9964 (0.6); 4.9566 (2.1); 4.9299 (2.1); 4.8899 (0.6); 4.2824 (0.9); 4.2726 (1.0); 4.2586 (1.0); 3.6951 (1.3); 3.6829 (1.4); 3.6710 (1.2); 3.6192 (0.8); 3.6090 (1.2); 3.6035 (1.0); 3.5968 (1.9); 3.5318 (1.9); 3.5196 (4.4); 3.5090 (0.9); 3.3750 (11.3); 1.5380 (16.0); 0.0080 (1.2); -0.0002 (47.6); -0.0085 (1.5) 1 H-NMR (400.0 MHz, CDCl 3 ): 5 = 7.7686 (1.5); 7.7620 (1.5); 7,3987 (1.4); 7.3767 (1.4); 7.2601 (36.0); 7.1037 (0.8); 7.0972 (0.8); 7.0835 (0.9); 7.0769 (0.8); 7.0058 (1.3); 6.9895 (1.3); 6.3117 (2.3); 4.9964 (0.6); 4.9566 (2.1); 4.9299 (2.1); 4.8899 (0.6); 4.2824 (0.9); 4.2726 (1.0); 4.2586 (1.0); 3.6951 (1.3); 3.6829 (1.4); 3.6710 (1.2); 3.6192 (0.8); 3.6090 (1.2); 3.6035 (1.0); 3.5968 (1.9); 3.5318 (1.9); 3.5196 (4.4); 3,5090 (0.9); 3.3750 (11.3); 1.5380 (16.0); 0.0080 (1.2); -0.0002 (47.6); -0.0085 (1.5)
Gegenstand der vorliegenden Erfindung ist weiterhin die Verwendung einer oder mehrerer The present invention also relates to the use of one or more
erfindungsgemäßer Verbindungen der allgemeinen Formel (I) und/oder deren Salze, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.36) und/oder deren Salze, jeweils wie oben definiert, inventive compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts , each as defined above,
als Herbizid und/oder Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen. as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.
Gegenstand der vorliegenden Erfindung ist ferner ein Verfahren zur Bekämpfung von Schadpflanzen und/oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer erfindungsgemäßer Verbindungen der allgemeinen Formel (I) und/oder deren Salze, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.36) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, auf die (Schad)Pflanzen, (Schad)Pflanzensamen, den Boden, in dem oder auf dem die (Schad)Pflanzen wachsen, oder die Anbaufläche appliziert wird. The present invention also relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) according to the invention and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, to the (harmful) Plants, (harmful) plant seeds, the soil in which or on which the (harmful) plants grow or the area under cultivation is applied.
Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen, vorzugsweise in Nutzpflanzenkulturen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salze, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten The present invention also relates to a method for controlling undesirable plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferred or particularly preferred
Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.36) und/oder deren Salze, jeweils wie oben definiert, oder eines erfmdungsgemäßen Mittels, wie nachstehend definiert, auf unerwünschte Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut der unerwünschten Pflanzen (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die unerwünschte Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die unerwünschte Pflanzen wachsen werden) appliziert wird. Design, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, on undesirable plants (for example harmful plants such as monocotyledon or dicotyledon weeds or undesired crop plants), the seeds of the undesired plants (ie plant seeds, for example grains, seeds or vegetative reproductive organs such as tubers or parts of shoots with buds), the Soil in which or on which the undesired plants grow (for example the soil of cultivated land or non-cultivated land) or the cultivated area (ie area on which the undesired plants will grow) is applied.
Gegenstand der vorliegenden Erfindung ist ferner auch Verfahren zur Bekämpfung zur The present invention also relates to methods of combating
Wachstumsregulierung von Pflanzen, vorzugsweise von Nutzpflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Growth regulation of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of those identified as preferred or particularly preferred
Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.36) und/oder deren Salze, jeweils wie oben definiert, oder eines erfmdungsgemäßen Mittels, wie nachstehend definiert, die Pflanze, das Saatgut der Pflanze (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Design, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, the plant, the seeds of the plant (ie plant seeds, e.g. grains, Seeds or vegetative
Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die Pflanzen wachsen werden) appliziert wird. Reproductive organs such as tubers or sprouts with buds), the soil in which or on which the plants grow (e.g. the soil of cultivated land or non-cultivated land) or the cultivated area (i.e. the area on which the plants will grow) is applied.
Dabei können die erfmdungsgemäßen Verbindungen bzw. die erfmdungsgemäßen Mittel z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- und/oder Nachauflaufverfahren ausgebracht werden. Im Einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen The compounds according to the invention or the agents according to the invention can be applied, for example, by pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or post-emergence methods. Some representatives of the monocotyledons and dicots are examples
Unkrautflora genannt, die durch die die erfmdungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Weed flora called, through which the compounds according to the invention can be controlled, without the mentioning of them being intended to restrict to certain species.
Vorzugsweise werden in einem erfmdungsgemäßen Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung in Kulturen von Nutzpflanzen oder Zierpflanzen eingesetzt, wobei die Nutzpflanzen oder Zierpflanzen in einer bevorzugten Ausgestaltung transgene Pflanzen sind. Die erfmdungsgemäßen Verbindungen allgemeinen Formel (I) und/oder deren Salze eignen sich zur Bekämpfung der folgenden Gattungen von monokotylen und dikotylen Schadpflanzen: In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamentals, the useful plants or ornamentals in a preferred embodiment are transgenic plants. The compounds of general formula (I) according to the invention and / or their salts are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragloaim, Festylochata , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Schadpflanzen der Gatungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicot harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, , Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumexio, Salsola, Senec , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Werden die erfmdungsgemäßen Verbindungen vor dem Keimen der Schadpflanzen (Ungräser und/oder Unkräuter) auf die Erdoberfläche appliziert (VorauflaufVerfahren), so wird entweder das Auflaufen der Ungras- bzw. Unkrautkeimlinge vollständig verhindert oder diese wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. If the compounds according to the invention are applied to the surface of the earth (pre-emergence method) before the harmful plants (weeds and / or weeds) germinate, either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage, but then continue to grow and finally die off completely after three to four weeks.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im NachauflaufVerfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. When the active ingredients are applied to the green parts of the plant using the post-emergence method, growth arrests after the treatment and the harmful plants remain in the growth stage present at the time of application or die completely after a certain time, so that in this way competition from weeds that is harmful to the crop plants is very early and is permanently eliminated.
Obgleich die erfmdungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,Although the compounds according to the invention have excellent herbicidal activity against monocotyledon and dicotyledon weeds, crops of economically important crops, for example dicotyledon crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, abhängig von der Struktur der jeweiligen erfmdungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie Pisum, Solanum, Vicia, or monocotyledon cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound according to the invention and the amount used, only insignificant or not damaged at all. For these reasons, the present compounds are very suitable for the selective control of undesired vegetation in plant crops such as
landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Darüberhinaus weisen die erfmdungsgemäßen Verbindungen (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Emteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. agricultural crops or ornamental crops. In addition, the compounds according to the invention (depending on their particular structure and the amount applied) have excellent growth-regulatory properties in crop plants. They intervene in a regulating manner in the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesired vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledon and dicotyledon crops, since it can reduce or completely prevent storage, for example.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered plants or plants that have been modified by conventional mutagenesis. The transgenic plants are generally distinguished by particularly advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate, for example, to the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered starch quality or those with different
Fettsäurezusammensetzung des Emteguts bekannt. Fatty acid composition of the harvested material known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfmdungsgemäßen Verbindungen und/oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. With regard to transgenic crops, preference is given to using the compounds according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereals such as wheat, barley, rye, oats, millet, rice and maize or else crops of sugar beet, cotton, Soy, rapeseed, potato, tomato, pea and other vegetables.
Vorzugsweise können die erfmdungsgemäßen Verbindungen auch als Herbizide in The compounds according to the invention can preferably also be used as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Crops of useful plants are used which are resistant to the phytotoxic effects of herbicides or which have been made resistant by genetic engineering.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used for combating harmful plants in crops of known or still to be developed genetically modified plants. The transgenic plants are generally distinguished by particularly advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate, for example, to the crop in terms of quantity, Quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered starch quality or those with different
Fettsäurezusammensetzung des Emteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z.B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung hegen. Fatty acid composition of the harvested material known. Further special properties can be found in a tolerance or resistance to abiotic stressors e.g. heat, cold, drought, salt and ultraviolet radiation.
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Triticale, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. The use of the compounds of general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize, is preferred Cultures of sugar beet, cotton, soy, canola, potato, tomato, pea and other vegetables.
Vorzugsweise können die Verbindungen der allgemeinen Formel (I) als Herbizide in The compounds of the general formula (I) can preferably be used as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Crops of useful plants are used which are resistant to the phytotoxic effects of herbicides or which have been made resistant by genetic engineering.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist, for example, in classic ways
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden. Breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering.
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind dem Fachmann bekannt. Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z.B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art. For such genetic manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard procedures, e.g. base exchanges can be carried out, partial sequences can be removed or natural or synthetic sequences can be added. For connecting the DNA fragments
untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden. adapters or linkers can be attached to the fragments.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann The production of plant cells with reduced activity of a gene product can
beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. for example, achieved by expressing at least one corresponding antisense RNA, one sense RNA to achieve a cosuppression effect or expressing at least one appropriately constructed ribozyme that specifically cleaves transcripts of the abovementioned gene product.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA- Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. For this purpose, on the one hand, DNA molecules can be used that comprise the entire coding sequence of a gene product including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough, to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z.B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any desired compartment of the plant cell. However, in order to achieve the localization in a certain compartment, e.g. the coding region can be linked with DNA sequences which ensure the localization in a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be any plant
Pflanzenspezies handeln, d.h. sowohl monokotyle als auch dikotyle Pflanzen. Act as plant species, i.e. both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Thus, transgenic plants can be obtained which have altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or the expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z.B. Dicamba oder gegen Herbizide, die essentielle The compounds (I) according to the invention can preferably be used in transgenic crops which are essential against growth substances such as dicamba or against herbicides
Pflanzenenzyme, z.B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD) inhibit or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze als Herbizide zur Bekämpfung von Schadpflanzen in Kulturen von Nutz- oder Zierpflanzen, gegebenenfalls in transgenen Kulturpflanzen. When the active ingredients according to the invention are used in transgenic crops, in addition to the effects on harmful plants observed in other crops, effects that are specific to the application in the respective transgenic crop, for example a modified or specially expanded weed spectrum that can be controlled, often occur Application rates which can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crop plants. The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crops.
Bevorzugt ist die Verwendung in Getreide, dabei vorzugsweise Mais, Weizen, Gerste, Roggen, Hafer, Hirse, oder Reis, im Vor- oder Nachauflauf. Preference is given to using them in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, pre- or post-emergence.
Bevorzugt ist auch die Verwendung in Soja im Vor- oder Nachauflauf. Pre- or post-emergence use in soy is also preferred.
Die erfmdungsgemäße Verwendung zur Bekämpfung von Schadpflanzen oder zur The use according to the invention for controlling harmful plants or for
Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem der Wirkstoff der allgemeinen Formel (I) oder dessen Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird. Regulation of the growth of plants also includes the case in which the active ingredient of the general formula (I) or its salt is formed from a precursor substance (“prodrug”) only after it has been applied to the plant, in the plant or in the soil.
Gegenstand der Erfindung ist auch die Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salzen bzw. eines erfmdungsgemäßen Mittels (wie nachstehend definiert) (in einem Verfahren) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehreren Verbindungen der allgemeinen Formel (I) oder deren Salzen auf die Pflanzen (Schadpflanzen, ggf. zusammen mit den Nutzpflanzen) Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert. The invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts are applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in which or on which the plants grow, or the area under cultivation.
Gegenstand der Erfindung ist auch ein herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel The invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
(a) eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthält wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
Ausgestaltung, insbesondere eine oder mehrere Verbindungen der Formeln (1.1) bis (1.36) und/oder deren Salze, jeweils wie oben definiert, Design, in particular one or more compounds of the formulas (1.1) to (1.36) and / or their salts, in each case as defined above,
und and
(b) ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii): (b) one or more other substances selected from groups (i) and / or (ii):
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der(i) one or more further agrochemically active substances, preferably selected from
Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden (d.h. solche, die nicht der oben definierten Formel (I) entsprechen), Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. Group consisting of insecticides, acaricides, nematicides, other herbicides (ie those that do not correspond to the formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.
Die weiteren agrochemischen wirksamen Stoffe des Bestandteils (i) eines erfmdungsgemäßen Mittels sind dabei vorzugsweise ausgewählt aus der Gruppe der Stoffe, die in "The Pesticide Manual", 16th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 genannt sind. The further agrochemically active substances of component (i) of an agent according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
Ein erfindungsgemäßes herbizides oder pflanzenwachstumsregulierendes Mittel, umfasst vorzugsweise ein, zwei, drei oder mehr im Pflanzenschutz übliche Formulierungshilfsmittel (ii) ausgewählt aus der Gruppe bestehend aus Tensiden, Emulgatoren, Dispergiermitteln, Filmbildnem, Verdickungsmitteln, anorganischen Salzen, Stäubemitteln, bei 25 °C und 1013 mbar festen Trägerstoffen, vorzugsweise adsorptionsfähigen, granulierten Inertmaterialien, Netzmitteln, Antioxidationsmitteln, Stabilisatoren, Puffersubstanzen, Antischaummitteln, Wasser, organischen Lösungsmitteln, vorzugsweise bei 25 °C und 1013 mbar mit Wasser in jedem beliebigen Verhältnis mischbare organische Lösungsmittel. A herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) which are customary in crop protection and selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents which are miscible with water in any ratio at 25 ° C and 1013 mbar.
Die erfmdungsgemäßen Verbindungen (I) können in Form von Spritzpulvem, emulgierbaren The compounds (I) according to the invention can be emulsifiable in the form of wettable powders
Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und Concentrates, sprayable solutions, dusts or granules are used in the usual preparations. The invention therefore also relates to herbicidal and
pflanzenwachstumsregulierende Mittel, die Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthalten. Plant growth regulating agents which contain compounds of the general formula (I) and / or their salts.
Die Verbindungen der allgemeinen Formel (I) und/oder deren Salze können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, The compounds of the general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemico-physical parameters are given. Possible formulation options include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions ,
Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions,
Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Capsule suspensions (CS), dusts (DP), dressings, granulates for the litter and
Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Floor application, granules (GR) in the form of micro, spray, lift and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
Mikrokapseln und Wachse. Microcapsules and waxes.
Diese einzelnen Formulierungstypen und die Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind dem Fachmann bekannt, und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvente Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive These individual formulation types and the formulation auxiliaries such as inert materials, surfactants, solvents and other additives are known to the person skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen , "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvent Guide"; 2nd Ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents, "Chem. Publ. Co. Inc., NY 1964; Schoenfeldt," Surface active
Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler," Chemische Technologie ", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Wettable powders are preparations that are uniformly dispersible in water which, in addition to the active ingredient, besides a diluent or inert substance, also ionic and / or nonionic surfactants (wetting agents, dispersants), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, sodium ligninsulfonates, alkylbenzenesulfonates , 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid sodium or oleoylmethyltaurin acid sodium. To produce the wettable powders, the herbicidally active ingredients are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calcium-Salze wie Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of an ionic and / or nonionic type (emulsifiers). Examples of emulsifiers that can be used are: alkylarylsulfonic acid calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or
Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.
Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Suspension concentrates can be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if necessary, the addition of surfactants, such as those already listed above for the other types of formulation.
Emulsionen, z.B. Öl-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Emulsions, e.g. oil-in-water emulsions (EW), can be converted, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic
Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hersteilen. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Solvents and optionally surfactants, such as those already listed above for the other types of formulation, produce. Granules can either be produced by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material. Can also be appropriate
Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active ingredients are granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischem und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally produced by the customary processes such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulaten siehe z.B. Verfahren in "Spray- Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. For the production of plate, fluidized bed, extruder and spray granules, see, for example, the method in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Ine., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. For further details on the formulation of plant protection products see e.g. G.C. Klingman, "Weed Control as a Science," John Wiley and Sons, Ine., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Die agrochemischen Zubereitungen, vorzugsweise herbizide oder pflanzenwachstumsregulierende Mittel der vorliegenden Erfindung enthalten vorzugsweise eine Gesamtmenge von 0,1 bis 99 Gew.-%, bevorzugt 0,5 bis 95 Gew.-%, weiter bevorzugt 1 bis 90 Gew.-%, insbesondere bevorzugt 2 bis 80 Gew.-%, an Wirkstoffen der allgemeinen Formel (I) und deren Salzen. The agrochemical preparations, preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferred 2 to 80% by weight, of active ingredients of the general formula (I) and their salts.
In Spritzpulvem beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige In wettable powders, the active ingredient concentration is e.g. about 10 to 90% by weight, the remainder to 100% by weight consists of conventional formulation components. In the case of emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dusty
Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew. -% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten hegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Beispiele für Formulierungshilfsmittel sind unter anderem in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998) beschrieben. Formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight. In addition, the active ingredient formulations mentioned contain, if appropriate, the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and the Viscosity influencing agents. Examples of formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
Die Verbindungen der allgemeinen Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder The compounds of the general formula (I) or their salts can be used as such or in the form of their preparations (formulations) with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
Wachstumsregulatoren kombiniert eingesetzt werden, z.B. als Fertigformulierung oder als Growth regulators can be used in combination, e.g. as a finished formulation or as
Tankmischungen. Die Kombinationsformulierungen können dabei auf Basis der obengenannten Formulierungen hergestellt werden, wobei die physikalischen Eigenschaften und Stabilitäten der zu kombinierenden Wirkstoffe zu berücksichtigen sind. Tank mixes. The combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active ingredients to be combined.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat- Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. in Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 und der dort zitierten Literatur beschrieben sind. Combination partners for the compounds of the general formula (I) according to the invention in mixture formulations or in the tank mix are, for example, known active ingredients which act on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate- Synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as they are for example in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited there.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfindungsgemäßen Verbindungen (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den The selective control of harmful plants in crops of useful and ornamental plants is of particular interest. Although the compounds (I) according to the invention already have very good to sufficient selectivity in many crops, in principle in some crops and especially in the case of mixtures with other herbicides which are less selective, phytotoxicities can occur on the
Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. Cultivated plants occur. In this regard, combinations of compounds (I) according to the invention which contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest. The safeners, which are used in an antidoteic content, reduce the phytotoxic side effects of the herbicides / pesticides used, for example in economically important crops such as grain (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rape, cotton and soy, preferably grain.
Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der The weight ratio of herbicide (mixture) to safener generally depends on the
Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200: 1 bis 1:200, vorzugsweise 100: 1 bis 1: 100, insbesondere 20: 1 bis 1:20. Die Safener können analog den Verbindungen (I) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden. Application rate of herbicide and the effectiveness of the respective safener and can continue within Limits vary, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds (I) or mixtures thereof with further herbicides / pesticides and are provided and used as a finished formulation or tank mix with the herbicides.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid-Safener- Formulierungen gegebenenfalls in üblicher weise verdünnt z.B. bei Spritzpulvem, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. For use, the herbicide or herbicide-safener formulations in commercially available form are optionally diluted in the customary manner, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Preparations in dust form, soil granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der allgemeinen Formel (I) und/oder deren Salze. Die External conditions such as temperature, humidity etc. influence to a certain extent the application rate of the compounds of the general formula (I) and / or their salts. The
Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der allgemeinen Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. The application rate can vary within wide limits. For use as a herbicide for combating harmful plants, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence use.
Bei der Anwendung von Verbindungen der allgemeinen Formel (I) und/oder deren Salzen als When using compounds of the general formula (I) and / or their salts as
Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Ge samt- Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im Plant growth regulator, for example as a stalk shortener in crop plants, as they have been mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to the application in
Vorauflauf oder im Nachauflauf. Pre-emergence or post-emergence.
Die Applikation als Halmverkürzer kann in verschiedenen Stadien des Wachstums der Pflanzen erfolgen. Bevorzugt ist beispielsweise die Anwendung nach der Bestockung am Beginn des The application as a stalk shortener can take place in different stages of the growth of the plants. For example, use after tillering at the beginning of the
Längenwachstums . Growth in length.
Alternativ kommt bei der Anwendung als Pflanzenwachstumsregulator auch die Behandlung des Saatguts in Frage, welche die unterschiedlichen Saatgutbeiz- und Beschichtungstechniken einschließt. Die Aufwandmenge hängt dabei von den einzelnen Techniken ab und kann in Vorversuchen ermittelt werden. Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in erfindungsgemäßen Mitteln (z.B. Mischungsformulierungen oder im Tank-Mix) sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p- Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II oder Alternatively, when used as a plant growth regulator, the treatment of the seed, which includes the different seed dressing and coating techniques, is also possible. The application rate depends on the individual techniques and can be determined in preliminary tests. Combination partners for the compounds of the general formula (I) according to the invention in agents according to the invention (e.g. mixed formulations or in a tank mix) are, for example, known active ingredients which act on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or
Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 16th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 und dort zitierter Literatur beschrieben sind. Nachfolgend werden beispielhaft bekannte Herbizide oder Pflanzenwachstumsregulatoren genannt, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, wobei diese Wirkstoffe entweder mit ihrem "common name" in der englischsprachigen Variante gemäß International Organization for Standardization (ISO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche Protoporphyrinogen oxidase based, usable, as for example from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited there. Known herbicides or plant growth regulators that can be combined with the compounds according to the invention are mentioned below by way of example, these active ingredients either with their "common name" in the English-language variant according to the International Organization for Standardization (ISO) or with the chemical name or code number are designated. Everyone is always there
Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische Isomere umfaßt, auch wenn diese nicht explizit erwähnt sind. Use forms such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned.
Beispiele für solche herbiziden Mischungspartner sind: Examples of such herbicidal mixing partners are:
Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfüron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfüron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfüresate, bensulfüron, bensulfüron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac- sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2- Chlor-4-fluor-5 -[4-(3 -fluorpropyl)-4,5 -dihydro-5 -oxo- lH-tetrazol- 1 -yl] -phenyl] -ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfüron, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl ) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfüron, benulfüreson, beflubutamidate, benazolin, benazolin, benflubutamidate , bensulfüron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-potano, -butyrate, potassium busoxinone, butachlor, butafenacil, butamifos, butenachlor, butraline, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, ch lorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodeprop, clodinafop, clodyllop, clodyrlop-propaz cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine , -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium , daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl-1,2-oxazolidine-3 - one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-l, 2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- , dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprouralcarb, ethalfluron, ethametsulfuron, ethametsulfuron, ethalflurcarb ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, ie N- [2-chloro-4-fluoro-5 - [4- (3-fluoropropyl) -4,5-dihydro -5 -oxo- lH-tetrazol- 1 -yl] -phenyl] -ethanesulfonamide, F- 7967, ie 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -lH-benzimidazol-4-yl] - l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (lH, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M- isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl,
flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. 0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-l- methyl-3-(trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenolofen-butyl, flurenol, flurenolofen-butyl, -dimethylammonium and -fluoroglycethylammonium flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinuf-ammonium, glufosinate-sodium P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium and -trimesium, H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl- isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, ie l- (Dimethoxyphosphoryl) -ethyl- (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazethapyrium, imazaquin- ammonium -immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, ieH 3 - ({[5- (difluoromethyl) -l-methyl-3- (trifluoromethyl) -lH-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1,2- oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium , and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione,
methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l -methyl - 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5 -[2-chlor-4-(trifluormethyl)phenoxy] -2-nitrobenzoat, SYP-300, i.e. 1 -[7 -Fluor-3 -oxo-4-(prop-2-in- 1 - yl)-3 ,4-dihydro-2H- 1 ,4-benzoxazin-6-yl] -3 -propyl-2-thioxoimidazolidin-4,5 -dion, 2,3 ,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tef iryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulf iron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulf iron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulf iron, trifloxysulf iron-sodium, trifludimoxazin, trifluralin, triflusulf iron, triflusulfuron-methyl, tritosulf iron, urea Sulfate, vemolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron-ester, monosulfuron, ie, N- [3-chloron, monosulfuron -4- (1-methylethyl) -phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfiamine, propachlor, prydomometr, methyl, promisulfuron, primloroxulfuron, methyl propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyraszamfenzol, ethyl, pyrazam-pyrazoxy -isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxofsulam, quinclorac-quizalocalopac. quizalocalopac , quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, si mazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie l-ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5 - [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie 1 - [7 -fluoro-3-oxo-4- (prop-2-in-1-yl) -3 , 4-dihydro-2H-1, 4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron , tef iryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumetone, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulf iron, thifensulfuron-methyl, tria-tofenyrone, tria-tofenyzone , triasulf iron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulf iron, trifloxysulf iron-sodium, trifludimoxazin, trifluralin, triflusulf iron, triflusulfuron-methyl, tritosulf iron, urea sulfate, vemolate, XDE-848., , ie 3,4-dichloro-N- {2- [(4,6-dimeth oxypyrimidin-2-yl) oxy] benzyl} aniline, as well as the following compounds:
Figure imgf000109_0001
Figure imgf000109_0001
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Acibenzolar, acibenzolar-S-methyl, 5-Aminolävulinsäure, ancymidol, 6-benzylaminopurine, Examples of plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
Brassinolid, Catechin, chlormequat Chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat Chloride, 1-methylcyclopropene, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. Brassinolide, Catechin, chlormequat Chloride, cloprop, cyclanilide, 3- (Cycloprop-l-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probemonic acid azole, jasmonic acid , maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2- (l-naphthyl) acetamide, 1-naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole , N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
Ebenfalls als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) kommen beispielsweise die folgenden Safener in Frage: The following safeners are also suitable as combination partners for the compounds of the general formula (I) according to the invention:
S 1) Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate: S 1) Compounds from the group of heterocyclic carboxylic acid derivatives:
Sla) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (Sla), vorzugsweise Sl a ) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (Sl a ), preferably
Verbindungen wie l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure, Compounds such as l- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S 1-1) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; Ethyl l- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S 1-1) ("Mefenpyr-diethyl"), and related compounds, as described in WO -A-91/07874;
Slb) Derivate der Dichlorphenylpyrazolcarbonsäure (Slb), vorzugsweise Verbindungen wie Sl b ) derivatives of dichlorophenylpyrazole carboxylic acid (Sl b ), preferably compounds such as
l-(2,4-Dichlorphenyl)-5-methylpyrazol-3-carbonsäureethylester (Sl-2), ethyl l- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (Sl-2),
l-(2,4-Dichlorphenyl)-5-isopropylpyrazol-3-carbonsäureethylester (Sl-3), ethyl l- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (Sl-3),
1 -(2,4-Dichlorphenyl)-5 -( 1 , 1 -dimethyl-ethyl)pyrazol-3 -carbonsäureethylester (S 1 -4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind; 1 - (2,4-dichlorophenyl) -5 - (1,1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S 1 -4) and related compounds, as they are in EP-A-333131 and EP-A-269806 are described;
Slc) Derivate der l,5-Diphenylpyrazol-3-carbonsäure (Slc), vorzugsweise Verbindungen wie Sl c ) derivatives of l, 5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as
l-(2,4-Dichlorphenyl)-5-phenylpyrazol-3 -carbonsäureethylester (Sl-5), ethyl l- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5),
l-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (Sl-6) und verwandte L- (2-Chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related
Verbindungen wie sie beispielsweise in der EP-A -268554 beschrieben sind; Compounds as described, for example, in EP-A-268554;
Sld) Verbindungen vom Typ der Triazolcarbonsäuren (Sld), vorzugsweise Verbindungen wie Sl d ) compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
Fenchlorazol(-ethylester), d.h. l-(2,4-Dichlorphenyl)-5-trichlormethyl-(lH)-l,2,4-triazol-3- carbonsäureethylester (Sl-7), und verwandte Verbindungen, wie sie in EP-A-174562 und EP-A-346620 beschrieben sind; Fenchlorazole (ethyl ester), i.e. l- (2,4-dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3- ethyl carboxylate (Sl-7), and related compounds, as described in EP-A-174562 and EP-A-346620;
Sle) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure(Sle), vorzugsweise Verbindungen wie Sl e ) compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S 1-8) oder 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S 1-8) or
5 -Phenyl-2-isoxazolin-3 -carbonsäureethylester (Sl-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-carbonsäure (S 1-10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester (Sl-11) ("Isoxadifen-ethyl") 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S 1- 10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-11) ("isoxadifen-ethyl")
oder -n-propylester (Sl-12) oder 5 -(4-Fluorphenyl)-5 -phenyl -2 -isoxazolin-3 -carbon säureethylester (S 1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind. or -n-propyl ester (S1-12) or 5 - (4-fluorophenyl) -5-phenyl -2 -isoxazoline-3-carbonic acid ethyl ester (S 1-13), as described in the patent application WO-A-95/07897 are described.
52) Verbindungen aus der Gruppe der 8-Chinolinoxyderivate (S2): 52) Compounds from the group of the 8-quinolinoxy derivatives (S2):
S2a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise S2 a ) compounds of the 8-quinolineoxyacetic acid type (S2 a ), preferably
(5-Chlor-8-chinolinoxy)essigsäure-(l-methylhexyl)-ester ("Cloquintocet-mexyl") (S2-1), (5-Chlor-8-chinolinoxy)essigsäure-(l,3-dimethyl-but-l-yl)-ester (S2-2), (5-Chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but -l-yl) ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester (S2-3), (5-chloro-8-quinolinoxy) acetic acid-4-allyl-oxy-butyl ester (S2-3),
(5-Chlor-8-chinolinoxy)essigsäure-l-allyloxy-prop-2-ylester (S2-4), (5-chloro-8-quinolinoxy) acetic acid-l-allyloxy-prop-2-yl ester (S2-4),
(5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5), (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5),
(5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6),
(5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7), (5-chloro-8-quinolinoxy) acetic acid allyl ester (S2-7),
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-l-ethylester (S2-8), (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-l-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind; (5-Chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366 are described, and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum , Iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34048;
S2b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise S2 b ) compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ), preferably
Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, Compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester,
(5-Chlor-8-chinolinoxy)malonsäurediallylester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind. (5-chloro-8-quinolinoxy) malonic acid methyl-ethyl ester and related compounds, as described in EP-A-0 582 198.
53) Wirkstoffe vom Typ der Dichloracetamide (S3), die häufig als Vorauflaufsafener 53) Active ingredients of the dichloroacetamide type (S3), which are often used as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z. B. (soil effective safeners) are used, such as. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1), "R-29148" (3-Dichloracetyl-2,2,5-trimethyl-l,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,-dimethyl-l,3-oxazolidin) der Firma Stauffer (S3-3), "Dichlormid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin) (S3-4), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
"PPG-1292" (N-Allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG "PPG-1292" (N-Allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide) from PPG
Industries (S3-5), Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6), "DKA-24" (N-Allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-l-oxa-3-aza-spiro[4,5]decan) der Firma "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4.5] decane) from the company
Nitrokemia bzw. Monsanto (S3-7), Nitrokemia or Monsanto (S3-7),
"TI-35" (1-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8), "TI-35" (1-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9) "Diclonon" (Dicyclonon) or "BAS145138" or "LAB145138" (S3-9)
((RS)-l-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10), sowie dessen (R)-Isomer (S3-11). ((RS) -l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [l, 2-a] pyrimidin-6-one) from BASF, "Furilazol" or "MON 13900" ((RS) -3-dichloroacetyl- 5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10) and its (R) -isomer (S3-11).
S4) Verbindungen aus der Klasse der Acylsulfonamide (S4): S4) Compounds from the class of the acylsulfonamides (S4):
S4a) N-Acylsulfonamide der Formel (S4a) und deren Salze wie sie in der WO-A-97/45016 S4 a ) N-acylsulfonamides of the formula (S4 a ) and their salts as described in WO-A-97/45016
beschrieben sind, are described
Figure imgf000112_0001
worin
Figure imgf000112_0001
wherein
RA 1 (Ci-Cö)-Alkyl, (C3-C6)-Cycloalkyl, wobei die 2 letztgenannten Reste durch VA R A 1 (Ci-C ö ) -alkyl, (C3-C6) -cycloalkyl, where the last two radicals mentioned by VA
Substituenten aus der Gruppe Halogen, (Ci-C- -Alkoxy, (Ci-Ce)-Haloalkoxy und (Ci- C4)-Alkylthio und im Falle cyclischer Reste auch durch (Ci-Cz -Alkyl und (C1-C4)- Haloalkyl substituiert sind; Substituents from the group halogen, (Ci-C- alkoxy, (Ci-Ce) -haloalkoxy and (Ci-C4) -alkylthio and in the case of cyclic radicals also by (Ci-Cz-alkyl and (C1-C4) -haloalkyl are substituted;
RA 2 Halogen, (Ci-C4)-Alkyl, (Ci-C4)-Alkoxy, CF3; mA 1 oder 2; R A 2 halogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkoxy, CF 3; m A 1 or 2;
VA ist 0, 1, 2 oder 3 bedeuten; S4b) Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze, wie sie in der WO-A-99/16744 beschrieben sind, VA is 0, 1, 2 or 3; S4 b ) compounds of the 4- (benzoylsulfamoyl) benzamide type of the formula (S4 b ) and their salts, as described in WO-A-99/16744,
Figure imgf000113_0001
worin
Figure imgf000113_0001
wherein
RB 1, RB 2 unabhängig voneinander Wasserstoff, (Ci-Ce)-Alkyl, (C3-C6)-Cycloalkyl, (CVG,)- Alkenyl, ( -G,)-Alkinyl. R B 1 , R B 2 independently of one another are hydrogen, (Ci-Ce) -alkyl, (C3-C6) -cycloalkyl, (CVG,) -alkenyl, (-G,) -alkynyl.
RB 3 Halogen, (Ci-G)-Alkyl, (Ci-C4)-Haloalkyl oder (Ci-G)-Alkoxy und mB 1 oder 2 bedeuten, z.B. solche worin R B 3 halogen, (Ci-G) -alkyl, (Ci-C4) -haloalkyl or (Ci-G) -alkoxy and m B 1 or 2, for example those in which
RB 1 = Cyclopropyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist ("Cyprosulfamide", S4-1), R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe ("Cyprosulfamide", S4-1),
RB 1 = Cyclopropyl, RB 2 = Wasserstoff und (RB 3) = 5-Cl-2-OMe ist (S4-2), R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-2),
RB 1 = Ethyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist(S4-3), R B 1 = ethyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe is (S4-3),
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB 3) = 5-Cl-2-OMe ist (S4-4) und R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-4) and
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist (S4-5); R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe (S4-5);
S4C) Verbindungen aus der Klasse der Benzoylsulfamoylphenylhamstoffe der Formel (S4C), wie sie in der EP-A-365484 beschrieben sind, S4 C ) compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4 C ), as described in EP-A-365484,
Figure imgf000113_0002
worin
Figure imgf000113_0002
wherein
Rc1, Rc2 unabhängig voneinander Wasserstoff, (G-G)-Alkyl, (G-G)-Cycloalkyl, (G-Rc 1 , Rc 2 independently of one another are hydrogen, (GG) -alkyl, (GG) -cycloalkyl, (G-
C6)-Alkenyl, (Cs-CeJ-Alkinyl, C 6 ) -alkenyl, (Cs-CeJ-alkynyl,
Rc3 Halogen, (Ci-G -Alkyl, (Ci-C- -Alkoxy, CF3 und mc 1 oder 2 bedeuten; beispielsweise l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylhamstoff, Rc 3 halogen, (Ci-G -alkyl, (Ci-C- alkoxy, CF 3 and mc is 1 or 2; for example l- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylhamstoff, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
l-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylhamstoff; 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea;
S4d) Verbindungen vom Typ der N-Phenylsulfonylterephthalamide der Formel (S4d) und deren Salze, die z.B. bekannt sind aus CN 101838227, S4 d ) compounds of the N-phenylsulfonyl terephthalamide type of the formula (S4 d ) and their salts, which are known, for example, from CN 101838227,
Figure imgf000114_0001
worin
Figure imgf000114_0001
wherein
RD4 Halogen, (Ci-C4)-Alkyl, (Ci-C4)-Alkoxy, CF3; mD 1 oder 2; RD 4 halogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkoxy, CF 3; m D 1 or 2;
RD5 Wasserstoff, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C5-RD 5 hydrogen, (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 5 -
C6)-Cycloalkenyl bedeutet. Is C 6 ) -cycloalkenyl.
55) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen 55) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic
Carbonsäurederivate (S5), z.B. Carboxylic acid derivatives (S5), e.g.
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoesäure, 3,5- Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4- Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO-A- 2005/016001 beschrieben sind. Ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A 2004/084631, WO-A-2005/015994, WO-A-2005/016001.
56) Wirkstoffe aus der Klasse der l,2-Dihydrochinoxalin-2-one (S6), z.B. 56) Active ingredients from the class of the 1,2-dihydroquinoxalin-2-ones (S6), e.g.
1 -Methyl-3 -(2-thienyl)- 1 ,2-dihydrochinoxalin-2-on, 1 -Methyl-3 -(2-thienyl)- 1 ,2-dihydro- chinoxalin-2-thion, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on-hydrochlorid, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on, wie sie in der WO- A-2005/112630 beschrieben sind. 1 -Methyl-3 - (2-thienyl) -1, 2-dihydroquinoxalin-2-one, 1 -methyl-3 - (2-thienyl) -1, 2-dihydroquinoxalin-2-thione, 1- (2 -Aminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxaline- 2-one, as described in WO-A-2005/112630.
57) Verbindungen aus der Klasse der Diphenylmethoxyessigsäurederivate (S7), z.B. 57) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g.
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1), Diphenylmethoxyessigsäureethylester oder Diphenylmethoxyessigsäure wie sie in der WO-A- 98/38856 beschrieben sind. Diphenylmethoxyacetic acid methyl ester (CAS Reg.Nr. 41858-19-9) (S7-1), Ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid as described in WO-A-98/38856.
S8) Verbindungen der Formel (S8), wie sie in der WO-A-98/27049 beschrieben sind, S8) compounds of the formula (S8) as described in WO-A-98/27049,
Figure imgf000115_0002
Figure imgf000115_0002
worin die Symbole und Indizes folgende Bedeutungen haben: where the symbols and indices have the following meanings:
RD1 ist Halogen, (Ci-C -Alkyl, (Ci-C- -Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, RD 1 is halogen, (Ci-C-alkyl, (Ci-C- haloalkyl, (Ci-C4) -alkoxy, (Ci-C4) -haloalkoxy,
RD 2 ist Wasserstoff oder (Ci-C4)-Alkyl, R D 2 is hydrogen or (Ci-C4) -alkyl,
RD3 ist Wasserstoff, (Ci-Cs)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; oder deren Salze, nD ist eine ganze Zahl von 0 bis 2. RD 3 is hydrogen, (Ci-Cs) -alkyl, (C2-C4) -alkenyl, (C2-C4) -alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts, n D is an integer from 0 to 2.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. S9) Active ingredients from the class of the 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
1 ,2-Dihydro-4-hydroxy- 1 -ethyl-3 -(5 -tetrazolylcarbonyl)-2-chinolon (CAS-Reg .Nr. : 219479-18- 2), l,2-Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 95855-00-8), wie sie in der WO-A- 1999/000020 beschrieben sind. 1,2-Dihydro-4-hydroxy- 1 -ethyl-3 - (5 -tetrazolylcarbonyl) -2-quinolone (CAS Reg .Nr.: 219479-18-2), 1,2-Dihydro-4-hydroxy- 1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS reg. no. 95855-00-8), as described in WO-A-1999/000020.
S10) Verbindungen der Formeln (S10a) oder (S10b), wie sie in der WO-A -2007/023719 und WO-A-2007/023764 beschrieben sind, worin S10) Compounds of the formulas (S10 a ) or (S10 b ), as described in WO-A -2007/023719 and WO-A-2007/023764, in which
Figure imgf000115_0001
Figure imgf000115_0001
RE1 Halogen, (Ci-C4)-Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 YE, ZE unabhängig voneinander O oder S, nE eine ganze Zahl von 0 bis 4, RE 1 halogen, (Ci-C4) -alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 Y E , Z E independently of one another O or S, n E is an integer from 0 to 4,
RE 2 (Ci-Ciö)-Alkyl, (CVCrd-Alkenyl. (C3-C6)-Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, R E 2 (Ci-Ci ö ) -alkyl, (CVCrd-alkenyl. (C3-C6) -cycloalkyl, aryl; benzyl, halobenzyl,
RE 3 Wasserstoff oder (C i-G,)-Alkyl bedeuten. R E 3 is hydrogen or (C iG,) - alkyl.
511) Wirkstoffe vom Typ der Oxyimino-Verbindungen (Si l), die als Saatbeizmittel bekannt sind, wie z. B. 511) Active ingredients of the type of oxyimino compounds (Si l), which are known as seed dressings, such as. B.
"Oxabetrinil" ((Z)-l,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (S 11-1), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, "Oxabetrinil" ((Z) -l, 3-Dioxolan-2-ylmethoxyimino (phenyl) acetonitril) (S 11-1), which is known as a seed dressing safener for millet against damage from metolachlor,
"Fluxofenim" ( 1 -(4-Chlorphenyl)-2,2,2-trifluor- 1 -ethanon-0-( 1 ,3 -dioxolan-2-ylmethyl)-oxim)"Fluxofenim" (1 - (4-chlorophenyl) -2,2,2-trifluoro-1-ethanon-0- (1,3-dioxolan-2-ylmethyl) -oxime)
(S 11-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und (S 11-2), which is known as a seed pickling safener for millet against damage from metolachlor, and
"Cyometrinü" oder "CGA -43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (S 11-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. "Cyometrinü" or "CGA -43089" ((Z) -Cyanomethoxyimino (phenyl) acetonitrile) (S 11-3), which is known as a seed dressing safener for millet against damage from metolachlor.
512) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl-[(3-oxo-lH-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S12-1) und verwandte Verbindungen aus WO-A-1998/13361. 512) Active ingredients from the class of isothiochromanones (S12), such as methyl - [(3-oxo-lH-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS reg. No. 205121-04-6 ) (S12-1) and related compounds from WO-A-1998/13361.
513) Eine oder mehrere Verbindungen aus Gruppe (S13): 513) One or more compounds from group (S13):
"Naphthalic anhydrid" (1,8-Naphthalindicarbonsäureanhydrid) (S13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "Naphthalic anhydride" (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
"Fenclorim" (4, 6-Dichlor-2 -phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,
"Flurazole" (Benzyl-2-chlor-4-trifluormethyl-l,3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist, "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor,
"CL 304415" (CAS-Reg.Nr. 31541-57-8) "CL 304415" (CAS reg. No. 31541-57-8)
(4-Carboxy-3,4-dihydro-2H-l-benzopyran-4-essigsäure) (S13-4) der Firma American (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American
Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, Cyanamide, which is known as a safener for corn against damage from imidazolinones,
"MG 191" (CAS-Reg.Nr. 96420-72-3) (2-Dichlormethyl-2-methyl-l,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "MG 838" (CAS-Reg.Nr. 133993-74-5) "MG 191" (CAS Reg.Nr. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize, "MG 838" (CAS Reg. No. 133993-74-5)
(2-propenyl l-oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia "Disulfoton" (0,0-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), (2-propenyl l-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia "Disulfoton" (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
"Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (S13-8), "Dietholate" (O, O-Diethyl-O-phenylphosphorothioate) (S13-8),
"Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9). "Mephenate" (4-chlorophenyl methyl carbamate) (S13-9).
514) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. 514) Active ingredients which, in addition to a herbicidal effect against harmful plants, also have a safener effect on crop plants such as rice, such as. B.
"Dimepiperate" oder "MY-93" (,U- 1 -Methyl- 1 -phenylethyl-piperidin- 1 -carbothioat). das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Dimepiperate" or "MY-93" (, U-1 -methyl-1-phenylethyl-piperidine-1-carbothioate). known as a safener for rice against damage from the herbicide Molinate,
"Daimuron" oder "SK 23" (1-(1 -Methyl- l-phenylethyl)-3-p-tolyl-hamstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfüron bekannt ist, "Daimuron" or "SK 23" (1- (1 -Methyl- l-phenylethyl) -3-p-tolyl-urea), which is known as a safener for rice against damage by the herbicide imazosulfüron,
"Cumyluron" = "JC-940" (3-(2-Chlorphenylmethyl)-l-(l-methyl-l-phenyl-ethyl)hamstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -l- (l-methyl-l-phenyl-ethyl) urea, see JP-A-60087254), which is used as a safener for rice against the damage of some herbicides is known
"Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against the damage of some herbicides,
"CSB" (l-Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091-06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. "CSB" (1-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.
515) Verbindungen der Formel (S15) oder deren Tautomere, 515) compounds of the formula (S15) or their tautomers,
Figure imgf000117_0001
Figure imgf000117_0001
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind, worin as described in WO-A-2008/131861 and WO-A-2008/131860, wherein
RH 1 einen (C C6)-Haloalkylrest bedeutet und R H 1 denotes a (CC 6 ) -haloalkyl radical and
RH 2 Wasserstoff oder Halogen bedeutet und R H 2 is hydrogen or halogen and
RH 3, RH 4 unabhängig voneinander Wasserstoff, (Ci-Cie)-Alkyl, (C2-Cie)-Alkenyl oder (C2-C16)-R H 3 , R H 4 independently of one another are hydrogen, (Ci-Cie) -alkyl, (C2-Cie) -alkenyl or (C2-C16) -
Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, [(Ci-C4)-Alkoxy]- carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (G-G)-Cycloalkyl. das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, oder (G-Cöj-Cycloalkyl, (CrCöj-Cycloalkenyl, (G-Gj-Cycloalkyl. das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)-Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6- gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (G-G)-Haloalkoxy. (G-G)-Alkylthio. (G-G)-Alkylamino. Di[(Ci- C4)alkyl]-amino, [(Ci-C4)Alkoxy]-carbonyl, [(Ci-C4)Haloalkoxy]-carbonyl, (G-CÖ)- Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, bedeutet oder Alkynyl, where each of the last-mentioned 3 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, ( Ci-C 4) alkylamino, di [(Ci-C4) -alkyl] amino, [(Ci-C 4) alkoxy] - carbonyl, [(Ci-C4) -haloalkoxy] carbonyl, (GG) Cycloalkyl. which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, is substituted, or (GC ö j-cycloalkyl, (CrC ö j-cycloalkenyl, (G-Gj-cycloalkyl. das an one side of the ring is condensed with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 ) -cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring , where each of the last-mentioned 4 radicals is unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) -alkoxy, (GG) -Haloalkoxy. (GG) -Alkylthio. (GG) -Alkylamino. Di [(Ci- C 4 ) alkyl] -amino, [(Ci-C 4 ) alkoxy] -carbonyl, [(Ci-C 4 ) Haloalkoxy] carbonyl, (GC Ö ) - cycloalkyl that is unsubstituted or substituted, phenyl that is unsubstituted or substituted, and heterocyclyl that is unsubstituted or is substituted, is substituted, means or
RH3 (Ci-C4)-Alkoxy, (C2-C4)-Alkenyloxy, (C2-G,)-Alkinyloxy oder (C2-C4)-Haloalkoxy bedeutet und RH 3 is (Ci-C 4 ) -alkoxy, (C2-C 4 ) -alkenyloxy, (C2-G,) -alkinyloxy or (C2-C 4 ) -haloalkoxy and
RH 4 Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder R H 4 is hydrogen or (Ci-C 4 ) -alkyl or
RH3 und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen RH 3 and RH 4 together with the directly bonded nitrogen atom form a four- to eight-membered
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (Ci- C4)-Alkyl, (Ci-G -Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy und (Ci-C4)-Alkylthio substituiert ist, bedeutet. heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, (Ci- C 4 ) -alkyl, (Ci-G-haloalkyl, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy and (Ci-C 4 ) -alkylthio is substituted.
S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z. B. S16) Active ingredients that are primarily used as herbicides, but also have a safener effect on crops, e.g. B.
(2,4-Dichlorphenoxy)essigsäure (2,4-D), (2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-Chlorphenoxy)essigsäure, (4-chlorophenoxy) acetic acid,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop), (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (Mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB), (4-Chlor-o-tolyloxy)essigsäure (MCPA), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxy) acetic acid (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure, 4- (4-chloro-o-tolyloxy) butyric acid,
4-(4-Chlorphenoxy)buttersäure, 4- (4-chlorophenoxy) butyric acid,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba), 3,6-dichloro-2-methoxybenzoic acid (Dicamba),
l-(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl). 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).
Bevorzugte Safener in Kombination mit den erfmdungsgemäßen Verbindungend der allgemeinen Formel (I) und/oder deren Salze, insbesondere mit den Verbindungen der Formeln (E 1) bis (1.34) und/oder deren Salze sind: Cloquintocet-mexyl, Cyprosulfamid, Fenchlorazol-ethylester, Isoxadifen- ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 und S4-5, und besonders bevorzugte Safener sind: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl und Mefenpyr-diethyl. Preferred safeners in combination with the compounds of the general formula (I) according to the invention and / or their salts, in particular with the compounds of the formulas (E 1) to (1.34) and / or their salts, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl ester , Isoxadifen-ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 and S4-5, and particularly preferred safeners are: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl and Mefenpyr-Diethyl.
Biologische Beispiele: Biological examples:
A. Herbizide Wirkung und Kulturverträglichkeit im Nachauflauf A. Herbicidal effects and post-emergence crop tolerance
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen wurden in Kunststoff- oder Seeds of monocotyledonous or dicotyledonous weed or crop plants were in plastic or
Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfmdungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Wooden fiber pots are laid out in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated in the single-leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of 600 l / ha. After the
Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Test plants in the greenhouse, under optimal growth conditions, the effect of the preparations was rated visually in comparison with untreated controls. For example, 100% activity means = plants have died, 0% activity = like control plants.
In den nachstehenden Tabllen Al bis A15 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.36 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 20 g/ha und niedriger, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Tabelle Al Tables A1 to A15 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 on various harmful plants and an application rate corresponding to 20 g / ha and lower, which were obtained according to the aforementioned test procedure. Table Al
Figure imgf000120_0001
Figure imgf000121_0001
Figure imgf000120_0001
Figure imgf000121_0001
Tabelle A2
Figure imgf000121_0002
Figure imgf000122_0001
Tabelle A3 Table A2
Figure imgf000121_0002
Figure imgf000122_0001
Table A3
Figure imgf000123_0001
Figure imgf000124_0001
Figure imgf000123_0001
Figure imgf000124_0001
Tabelle A4
Figure imgf000124_0002
Figure imgf000125_0001
Figure imgf000126_0001
Table A4
Figure imgf000124_0002
Figure imgf000125_0001
Figure imgf000126_0001
Tabelle A5 Table A5
Figure imgf000127_0001
Figure imgf000128_0001
Figure imgf000127_0001
Figure imgf000128_0001
Tabelle A6
Figure imgf000128_0002
Figure imgf000129_0001
Table A6
Figure imgf000128_0002
Figure imgf000129_0001
Tabelle A7
Figure imgf000129_0002
Figure imgf000130_0001
Figure imgf000131_0001
Table A7
Figure imgf000129_0002
Figure imgf000130_0001
Figure imgf000131_0001
Tabelle A8
Figure imgf000131_0002
Figure imgf000132_0001
Figure imgf000133_0001
Table A8
Figure imgf000131_0002
Figure imgf000132_0001
Figure imgf000133_0001
Tabelle A9
Figure imgf000133_0002
Figure imgf000134_0001
Figure imgf000135_0001
Table A9
Figure imgf000133_0002
Figure imgf000134_0001
Figure imgf000135_0001
Tabelle A10
Figure imgf000135_0002
Figure imgf000136_0001
Figure imgf000137_0001
Table A10
Figure imgf000135_0002
Figure imgf000136_0001
Figure imgf000137_0001
Tabelle All
Figure imgf000137_0002
Figure imgf000138_0001
Table All
Figure imgf000137_0002
Figure imgf000138_0001
Tabelle A12
Figure imgf000139_0001
Table A12
Figure imgf000139_0001
Tabelle A13
Figure imgf000139_0002
Figure imgf000140_0001
Figure imgf000141_0001
Table A13
Figure imgf000139_0002
Figure imgf000140_0001
Figure imgf000141_0001
Tabelle A14
Figure imgf000141_0002
Figure imgf000142_0001
Figure imgf000143_0001
Table A14
Figure imgf000141_0002
Figure imgf000142_0001
Figure imgf000143_0001
Tabelle A15
Figure imgf000143_0002
Table A15
Figure imgf000143_0002
In den nachstehenden Tabllen A16 bis A19 sind die Kulturverträglichkeiten ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.36 bei einer Aufwandmenge entsprechend 5 oder 20 g/ha, die bei Versuchen gemäß zuvor genannter Versuchvorschrift beobachtet wurden, dargestellt. Es werden dabei die beobachteten Effekte an ausgewählten Kulturpflanzen im Vergleich zu den unbehandelten Kontrollen angegeben (Werte in %). Tables A16 to A19 below show the crop compatibility of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 at an application rate corresponding to 5 or 20 g / ha, which were observed in tests according to the above-mentioned test procedure. The effects observed on selected crop plants are given in comparison with the untreated controls (values in%).
Tabelle A16 Table A16
Figure imgf000144_0001
Figure imgf000145_0001
Figure imgf000144_0001
Figure imgf000145_0001
Tabelle A17
Figure imgf000145_0002
Table A17
Figure imgf000145_0002
Tabelle Al 8
Figure imgf000145_0003
Table Al 8
Figure imgf000145_0003
Tabelle A19
Figure imgf000145_0004
Figure imgf000146_0001
Table A19
Figure imgf000145_0004
Figure imgf000146_0001
Wie die Ergebnisse zeigen, weisen erfmdungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf wie z. B. As the results show, compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants, such as, for example, on post-emergence treatment. B.
Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica und Viola tricolor bei einer Aufwandmenge von 0,02 kg Aktivsubstanz oder weniger pro Hektar, sowie eine gute Kulturpflanzenverträglichkeit bei Oganismen, wie Oryza sativa, Zea mays, Brassica napus und Triticum aestivum bei einer Aufwandmenge von 0.02 kg oder weniger pro Hektar. Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridica and Viola tricolorica, Stellaria media when applied at an amount of persistence 0.02 kg of active ingredient or less per hectare, as well as good tolerance to crop plants in organisms such as Oryza sativa, Zea mays, Brassica napus and Triticum aestivum at an application rate of 0.02 kg or less per hectare.
B. Herbizide Wirkung und Kulturverträglichkeit im Vorauflauf B. Herbicidal effect and pre-emergence crop tolerance
Samen von mono- bzw. dikotylen Unkraut und Kulturpflanzen wurden in Kunststoff- oder organischen Pflanztöpfen ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfmdungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca. 3 Wochen wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants were placed in plastic or organic plant pots and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of the equivalent of 600 l / ha. After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was rated visually in percentage values in comparison with untreated controls. For example, 100% activity means = plants have died, 0% activity = like control plants.
In den nachstehenden Tabllen Bl bis B 13 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.36 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 80 g/ha oder niedriger, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Tables B1 to B 13 below show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 on various harmful plants and one Application rate corresponding to 80 g / ha or lower, which was obtained according to the test procedure mentioned above, is shown.
Tabelle Bl Table Bl
Figure imgf000147_0001
Figure imgf000147_0001
Tabelle B2
Figure imgf000148_0001
Table B2
Figure imgf000148_0001
Tabelle B3
Figure imgf000148_0002
Figure imgf000149_0001
Table B3
Figure imgf000148_0002
Figure imgf000149_0001
Tabelle B4
Figure imgf000149_0002
Table B4
Figure imgf000149_0002
Tabelle B5
Figure imgf000149_0003
Figure imgf000150_0001
Table B5
Figure imgf000149_0003
Figure imgf000150_0001
Tabelle B6 Table B6
Figure imgf000150_0002
Figure imgf000150_0002
Tabelle B7
Figure imgf000150_0003
Figure imgf000151_0001
Table B7
Figure imgf000150_0003
Figure imgf000151_0001
Tabelle B8
Figure imgf000151_0002
Tabelle B9
Figure imgf000152_0001
Table B8
Figure imgf000151_0002
Table B9
Figure imgf000152_0001
Tabelle BIO
Figure imgf000152_0002
Figure imgf000153_0001
Table BIO
Figure imgf000152_0002
Figure imgf000153_0001
Tabelle Bll
Figure imgf000153_0002
Table Bll
Figure imgf000153_0002
Tabelle B 12
Figure imgf000153_0003
Figure imgf000154_0001
Table B 12
Figure imgf000153_0003
Figure imgf000154_0001
Tabelle B 13
Figure imgf000154_0002
In den nachstehenden Tabllen B14 bis B16 sind die Kulturverträglichkeiten ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.36 bei einer Aufwandmenge entsprechend 20 g/ha, die bei Versuchen gemäß zuvor genannter Versuchvorschrift beobachtet wurden, dargestellt. Es werden dabei die beobachteten Effekte an ausgewählten Kulturpflanzen im Vergleich zu den unbehandelten Kontrollen angegeben (Werte in %). Table B 13
Figure imgf000154_0002
Tables B14 to B16 below show the crop compatibility of selected compounds of the general formula (I) according to Tables 1.1 to 1.36 at an application rate corresponding to 20 g / ha, which were observed in tests according to the above test procedure. The effects observed on selected crop plants are given in comparison with the untreated controls (values in%).
Tabelle B 14 Table B 14
Figure imgf000155_0001
Tabelle B 15
Figure imgf000155_0001
Table B 15
Figure imgf000155_0002
Figure imgf000155_0002
Tabelle B 16 Table B 16
Figure imgf000156_0001
Figure imgf000156_0001
Wie die Ergebnisse zeigen, weisen erfmdungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Vorauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf, z. B. gegenAs the results show, compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants when treated pre-emergence, eg. B. against
Schadpflanzen wie Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Veronica persica und Viola tricolor bei einer Aufwandmenge von 0.08 kg Aktivsubstanz oder weniger pro Hektar, , sowie eine gute Kulturpflanzenverträglichkeit bei Oganismen, wie Zea mays, Glycine max und Triticum aestivum bei einer Aufwandmenge von 0.02 kg pro Hektar. Harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Veronica tricolorica or an active substance of 0.0 kg less per hectare, as well as a good tolerance to crop plants in organisms such as Zea mays, Glycine max and Triticum aestivum at an application rate of 0.02 kg per hectare.

Claims

Patentansprüche: Patent claims:
1 Substituierte N-Phenyluracile der allgemeinen Formel (I) oder deren Salze 1 Substituted N-phenyluracils of the general formula (I) or their salts
Figure imgf000157_0001
Figure imgf000157_0001
worin wherein
R1 für Wasserstoff, (Ci-Cs)-Haloalkyl steht, R 1 represents hydrogen, (Ci-Cs) -haloalkyl,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, (Ci-Cs)-Alkoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-Cs) -alkoxy,
R3 für Wasserstoff, Halogen, (Ci-Cs)-Alkoxy steht, R 3 represents hydrogen, halogen, (Ci-Cs) -alkoxy,
R4 für Halogen, Cyano, NO2, C(0)NH2, C(S)NH2, (Ci-Cs)-Haloalkyl, (C2-C8)-Alkinyl steht, R 4 represents halogen, cyano, NO2, C (0) NH 2 , C (S) NH2, (Ci-Cs) -haloalkyl, (C2-C 8 ) -alkynyl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (Ci-Cs)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-Cs)-Alkoxy, (Ci-Cs)-Haloalkoxy stehen, R 5 , R 6 and R 7 independently represent hydrogen, halogen, cyano, (Ci-Cs) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-Cs) -alkoxy, (Ci-Cs) -haloalkoxy ,
G für unverzweigtes oder verzweigtes (Ci-C8)-Alkylen steht, G is unbranched or branched (Ci-C 8 ) -alkylene,
Q für einen Rest der Formel
Figure imgf000157_0002
steht, Q for a remainder of the formula
Figure imgf000157_0002
stands,
R8 für Wasserstoff, (Ci-Cg)-Alkyl, (Ci-Cs)-Haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Alkyl R 8 is hydrogen, (Ci-Cg) alkyl, (Ci-Cs) -haloalkyl, aryl, aryl (Ci-C 8),
Heteroaryl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl, C(0)R13, C(0)0R13, (Ci-C8)-Alkoxy- (Ci-C8)-alkyl steht, Heteroaryl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -alkenyl, C (0) R 13 , C (0) OR 13 , (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl,
R9 für Wasserstoff oder (Ci-C8)-Alkyl steht, R10 für Cyano, NO2, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-R 9 represents hydrogen or (Ci-C 8 ) -alkyl, R 10 for cyano, NO2, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl, heterocyclyl-
(Ci-Cs)-alkyl, RnR12N-(Ci-C8)-alkyl, R130-(Ci-C8)-alkyl, Cyano-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyloxy-(Ci-C8)-alkyl, (C3-C8)-Cycloalkylcarbonyloxy-(Ci-C8)-alkyl, Arylcarbonyloxy-(Ci-C8)-alkyl, Heteroarylcarbonyloxy-(Ci-C8)-alkyl, (Ci-Cs) -alkyl, R n R 12 N- (Ci-C 8 ) -alkyl, R 13 0- (Ci-C 8 ) -alkyl, cyano- (Ci-C 8 ) -alkyl, (Ci- C 8 ) -alkylcarbonyloxy- (Ci-C 8 ) -alkyl, (C3-C 8 ) -cycloalkylcarbonyloxy- (Ci-C 8 ) -alkyl, arylcarbonyloxy- (Ci-C 8 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 8 ) -alkyl,
Heterocyclylcarbonyloxy-(Ci-C8)-alkyl, OR13, NRnR12, SR14, S(0)R14, S02R14, R14S- (Ci-C8)-alkyl, R14(0)S-(Ci-C8)-alkyl, R1402S-(Ci-C8)-alkyl, Tris-[(Ci-C8)-Alkyl]silyl- (Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl](aryl)silyl(Ci-C8)-alkyl, [(Ci-C8)-Alkyl]-bis- (aryl)silyl-(Ci-C8)-alkyl, Tris-[(Ci-C8)-Alkyl]silyl, Bis-hydroxyboryl-(Ci-C8)-alkyl, Bis- [(Ci-C8)-alkoxy]boryl-(Ci-C8)-alkyl, Tetramethyl- 1, 3, 2-Dioxaborolan-2-yl, Heterocyclylcarbonyloxy- (Ci-C 8 ) -alkyl, OR 13 , NR n R 12 , SR 14 , S (0) R 14 , S0 2 R 14 , R 14 S- (Ci-C 8 ) -alkyl, R 14 ( 0) S- (Ci-C 8 ) -alkyl, R 14 0 2 S- (Ci-C 8 ) -alkyl, tris - [(Ci-C 8 ) -alkyl] silyl- (Ci-C 8 ) -alkyl , Bis - [(Ci-C 8 ) -alkyl] (aryl) silyl (Ci-C 8 ) -alkyl, [(Ci-C 8 ) -alkyl] -bis- (aryl) silyl- (Ci-C 8 ) -alkyl, tris - [(Ci-C 8 ) -alkyl] silyl, bis-hydroxyboryl- (Ci-C 8 ) -alkyl, bis- [(Ci-C 8 ) -alkoxy] boryl- (Ci-C 8 ) -alkyl, tetramethyl-1, 3, 2-dioxaborolan-2-yl,
Tetramethyl-l,3,2-Dioxaborolan-2-yl-(Ci-C8)-alkyl, Nitro-(Ci-C8)-alkyl, C(0)R14, Bis- (Ci-C8)-alkoxymethyl, Bis-(Ci-C8)-alkoxymethyl-(Ci-C8)-alkyl steht, oder Tetramethyl-l, 3,2-dioxaborolan-2-yl- (Ci-C 8 ) -alkyl, nitro- (Ci-C 8 ) -alkyl, C (0) R 14 , bis- (Ci-C 8 ) - alkoxymethyl, bis- (Ci-C 8 ) -alkoxymethyl- (Ci-C 8 ) -alkyl, or
R8 und R10 mit dem Kohlenstoffatom, an das sie gebunden sind, ein vollständig gesättigtes oder teilgesättigtes, und gegebenenfalls weiter substituiertes 3 bis 10-gliedriges R 8 and R 10, with the carbon atom to which they are bonded, are a fully saturated or partially saturated, and optionally further substituted 3 to 10-membered one
monocyclisches oder bicyclisches Heterocyclyl bilden, form monocyclic or bicyclic heterocyclyl,
R11 und R12 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C8)- Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C3-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy- (Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl- (Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR13, S02R14, Heterocyclyl, (Ci-C8)- Alkoxycarbonyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkyl- aminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl-aminocarbonyl-(Ci-C8)-alkyl, Aryl- (Ci-C8)-alkoxycarbonyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl, (C2-C8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen, oder R 11 and R 12 are identical or different and are independently hydrogen, (Ci-C 8) - alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) -Cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C3-C10) -halocycloalkyl, (C4 -Cio) -Cycloalkenyl, (C4-Cio) -halocycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -Alkylthio- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkylthio- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, (C3-C 8 ) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 4 -Cio) -Cycloalkenyl- (Ci-C 8 ) -alkyl, COR 13 , S0 2 R 14 , heterocyclyl, (Ci-C 8 ) -alkoxycarbonyl, bis- [(Ci-C 8 ) -alkyl] aminocarbonyl- ( Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkyl aminocarbonyl- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkyl-aminocarbonyl- (Ci-C 8 ) -alkyl, Aryl- (Ci-C 8 ) -alkoxycarbonyl, heteroaryl- (Ci-C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, (C 2 -C 8 ) -Alkinyloxycarbonyl, heterocyclyl- (Ci-C 8 ) -alkyl, or
Rnund R12 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R n and R 12 with the nitrogen atom to which they are attached form a completely saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, optionally interrupted by heteroatoms and optionally further substituted,
R13 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C3-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- haloalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkoxy- (Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxy-(Ci-C8)- alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkyl-aminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl-aminocarbonyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(C2-C6)-alkyl, (Ci-C8)-Alkyl-amino-(C2-C6)-alkyl, Aryl-(Ci- C8)-alkyl-amino-(C2-C6)-alkyl, R14S-(Ci-C8)-alkyl, R14(0)S-(Ci-C8)-alkyl, R1402S- (Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)- alkyl, Tris-[(Ci-C8)-Alkyl]silyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl](aryl)silyl(Ci-C8)- alkyl, [(Ci-C8)-Alkyl]-bis-(aryl)silyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyloxy-(Ci-C8)- alkyl, (C3-C8)-Cycloalkylcarbonyloxy-(Ci-C8)-alkyl, Arylcarbonyloxy-(Ci-C8)-alkyl, Heteroarylcarbonyloxy-(Ci-C8)-alkyl, Heterocyclylcarbonyloxy-(Ci-C8)-alkyl, Aryloxy- (Ci-C8)-alkyl, Heteroaryloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl steht, R 13 for hydrogen, (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C3-C 8 ) -haloalkynyl, (C3-Cio) -cycloalkyl, (C3-Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4-Cio) - Halocycloalkenyl, (Ci-C 8 ) - Alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, (Ci- C 8 ) -Alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy - (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl , (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (C4-C10) - cycloalkenyl (Ci-C 8) alkyl, - bis [(Ci-C 8) alkyl] aminocarbonyl - (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkyl-aminocarbonyl- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkyl-aminocarbonyl- (Ci-C 8 ) - alkyl, bis [(Ci-C 8 ) -alkyl] amino- (C 2 -C 6 ) -alkyl, (Ci-C 8 ) -alkyl-amino- (C 2 -C 6 ) -alkyl, aryl- ( Ci- C 8 ) -alkyl-amino- (C 2 -C 6 ) -alkyl, R 14 S- (Ci-C 8 ) -alkyl, R 14 (0) S- (Ci-C 8 ) -alkyl, R 14 0 2 S- (Ci-C 8 ) -alkyl, hydroxycarbonyl- (Ci-C 8 ) -alkyl, heterocyclyl, heterocyclyl- (Ci-C 8 ) -alkyl, tris - [(Ci-C 8 ) -alkyl] silyl- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -A alkyl] (aryl) silyl (Ci-C 8 ) -alkyl, [(Ci-C 8 ) -alkyl] -bis- (aryl) silyl- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkylcarbonyloxy - (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkylcarbonyloxy- (Ci-C 8 ) -alkyl, arylcarbonyloxy- (Ci-C 8 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 8 ) -alkyl , Heterocyclylcarbonyloxy- (Ci-C 8 ) -alkyl, aryloxy- (Ci-C 8 ) -alkyl, heteroaryloxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxycarbonyl,
R14 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C3-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino, (Ci-C8)- Alkyl-amino, Aryl-(Ci-C8)-amino, Aryl-(Ci-C6)-alkyl-amino, Aryl-[(Ci-C8)- alkyl]amino; (C3-C8)-Cycloalkyl-amino, (C3-C8)-Cycloalkyl-[(Ci-C8)-alkyl]amino; N- Azetidinyl, N-Pyrrolidinyl, N-Piperidinyl. N-Morpholinyl, steht R 14 for hydrogen, (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 3 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C 4 -Cio) -cycloalkenyl, (C 4 -Cio) -halocycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci- C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) -alkyl, ( C 4 -Cio) -Cycloalkenyl- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -alkyl] amino, (Ci-C 8 ) -alkyl-amino, aryl- (Ci-C 8 ) -amino, aryl- (Ci-C 6 ) -alkyl-amino, aryl- [(Ci-C 8 ) -alkyl] amino; (C 3 -C 8 ) -cycloalkyl-amino, (C 3 -C 8 ) -cycloalkyl - [(Ci-C 8 ) -alkyl] amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl. N-morpholinyl
und and
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen. X and Y independently represent O (oxygen) or S (sulfur).
2. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 2. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that
R1 für Wasserstoff, (Ci-C6)-Haloalkyl steht, R 1 represents hydrogen, (Ci-C 6 ) -haloalkyl,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, (Ci-C6)-Alkoxy steht, R3 für Wasserstoff, Halogen, (Ci-C6)-Alkoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (Ci-C 6 ) -alkoxy, R 3 represents hydrogen, halogen, (Ci-C 6 ) -alkoxy,
R4 für Halogen, Cyano, NO2, C(0)NH2, C(S)NH2, (Ci-C7)-Haloalkyl, (C2-C7)-Alkinyl steht, R 4 represents halogen, cyano, NO2, C (0) NH 2 , C (S) NH 2 , (Ci-C7) -haloalkyl, (C 2 -C7) -alkynyl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (Ci-C7)-Alkyl, R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (Ci-C7) -alkyl,
(Ci-C7)-Haloalkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Haloalkoxy stehen, (Ci-C7) -haloalkyl, (Ci-C7) -alkoxy, (Ci-C7) -haloalkoxy,
G für unverzweigtes oder verzweigtes (Ci-C7)-Alkylen steht, G stands for unbranched or branched (Ci-C7) -alkylene,
Q für einen Rest der Formel
Figure imgf000160_0001
steht, Q for a remainder of the formula
Figure imgf000160_0001
stands,
R8 für Wasserstoff, (Ci-C7)-Alkyl, (Ci-C7)-Haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, R 8 for hydrogen, (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl,
Heteroaryl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl, C(0)R13, C(0)OR13, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl steht, Heteroaryl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl, C (0) R 13 , C (0) OR 13 , (Ci-C 7 ) -alkoxy- (Ci-C7) -alkyl stands,
R9 für Wasserstoff oder (Ci-G,)-Alkyl steht, R 9 represents hydrogen or (Ci-G,) - alkyl,
R10 für Cyano, N02, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-R 10 for cyano, N0 2 , heteroaryl, heteroaryl (Ci-C7) alkyl, heterocyclyl, heterocyclyl
(Ci-C7)-alkyl, RnR12N-(Ci-C7)-alkyl, R130-(Ci-C7)-alkyl, Cyano-(Ci-C7)-alkyl, (C1-C7)- Alkylcarbonyloxy-(Ci-C7)-alkyl, (C3-C7)-Cycloalkylcarbonyloxy-(Ci-C7)-alkyl, Arylcarbonyloxy-(Ci-C7)-alkyl, Heteroarylcarbonyloxy-(Ci-C7)-alkyl, (Ci-C 7 ) -alkyl, R n R 12 N- (Ci-C 7 ) -alkyl, R 13 0- (Ci-C 7 ) -alkyl, cyano- (Ci-C 7 ) -alkyl, (C1 -C7) - alkylcarbonyloxy- (Ci-C7) -alkyl, (C3-C7) -cycloalkylcarbonyloxy- (Ci-C7) -alkyl, arylcarbonyloxy- (Ci-C7) -alkyl, heteroarylcarbonyloxy- (Ci-C7) -alkyl,
Heterocyclylcarbonyloxy-(Ci-C7)-alkyl, OR13, NRnR12, SR14, S(0)R14, S02R14, R14S- (Ci-C7)-alkyl, R14(0)S-(Ci-C7)-alkyl, R1402S-(Ci-C7)-alkyl, Tris-[(Ci-C7)-Alkyl]silyl- (Ci-C7)-alkyl, Bis-[(Ci-C7)-Alkyl](aryl)silyl(Ci-C7)-alkyl, [(Ci-C7)-Alkyl]-bis- (aryl)silyl-(Ci-C7)-alkyl, Tris-[(Ci-C7)-Alkyl]silyl, Bis-hydroxyboryl-(Ci-C7)-alkyl, Bis- [(Ci-C7)-alkoxy]boryl-(Ci-C7)-alkyl, Tetramethyl- 1, 3, 2-Dioxaborolan-2-yl, Heterocyclylcarbonyloxy- (Ci-C 7 ) -alkyl, OR 13 , NR n R 12 , SR 14 , S (0) R 14 , S0 2 R 14 , R 14 S- (Ci-C 7 ) -alkyl, R 14 ( 0) S- (Ci-C 7 ) -alkyl, R 14 0 2 S- (Ci-C 7 ) -alkyl, tris - [(Ci-C 7 ) -alkyl] silyl- (Ci-C 7 ) -alkyl , Bis - [(Ci-C 7 ) -alkyl] (aryl) silyl (Ci-C 7 ) -alkyl, [(Ci-C 7 ) -alkyl] -bis- (aryl) silyl- (Ci-C7) - alkyl, tris - [(Ci-C7) -alkyl] silyl, bis-hydroxyboryl- (Ci-C7) -alkyl, bis- [(Ci-C7) -alkoxy] boryl- (Ci-C7) -alkyl, tetramethyl- 1, 3, 2-dioxaborolan-2-yl,
Tetramethyl-l,3,2-Dioxaborolan-2-yl-(Ci-C7)-alkyl, Nitro-(Ci-C7)-alkyl, C(0)R14, Bis- (Ci-C7)-alkoxymethyl, Bis-(Ci-C7)-alkoxymethyl-(Ci-C7)-alkyl steht, oder Tetramethyl-1,3,2-dioxaborolan-2-yl- (Ci-C 7 ) -alkyl, nitro- (Ci-C7) -alkyl, C (0) R 14 , bis- (Ci-C7) -alkoxymethyl, Bis- (Ci-C7) -alkoxymethyl- (Ci-C7) -alkyl, or
R8 und R10 mit dem Kohlenstoffatom, an das sie gebunden sind, ein vollständig gesättigtes oder teilgesättigtes, und gegebenenfalls weiter substituiertes 3 bis 10-gliedriges R 8 and R 10, with the carbon atom to which they are bonded, are a fully saturated or partially saturated, and optionally further substituted 3 to 10-membered one
monocyclisches oder bicyclisches Heterocyclyl bilden, R11 und R12 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C7)- Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C3-C7)-Haloalkinyl, (C3-Ci0)-Cycloalkyl, (C3-Ci0)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl- (Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, COR13, S02R14, Heterocyclyl, (Ci-C7)- Alkoxycarbonyl, Bis-[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkyl- aminocarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl-aminocarbonyl-(Ci-C7)-alkyl, Aryl- (Ci-C7)-alkoxycarbonyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C7)-alkyl stehen, oder form monocyclic or bicyclic heterocyclyl, R 11 and R 12 are identical or different and are independently hydrogen, (Ci-C7) - alkyl, (C 2 -C 7) alkenyl, (C2-C7) alkynyl, (Ci-C7) - Cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Ci 0 ) -cycloalkyl, (C 3 -Ci 0 ) -halocycloalkyl, (C4-Cio) -Cycloalkenyl, (C4-Cio) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) - alkyl, (Ci-C 7 ) -Alkylthio- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkylthio- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -Alkoxy- (Ci- C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (Ci-C 7 ) -alkyl , (C 4 -Cio) -Cycloalkenyl- (Ci-C 7 ) -alkyl, COR 13 , S0 2 R 14 , heterocyclyl, (Ci-C 7 ) -alkoxycarbonyl, bis - [(Ci-C 7 ) -alkyl] aminocarbonyl- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkyl- aminocarbonyl- (Ci-C 7 ) -alkyl, aryl- (Ci-C 7 ) -alkyl-aminocarbonyl- (Ci-C 7 ) -alkyl, aryl- (Ci-C 7 ) -alkoxycarbonyl, heteroaryl- (Ci-C 7 ) -alkoxycarbonyl, (C 2 -C 7 ) -alkenyloxycarbonyl, (C 2 -C 7 ) -alkinyloxycarbonyl, heterocyclyl- (Ci-C 7 ) -alkyl, or
Rn und R12 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gbedrigen monocyclischen oder bicyclischen Ring bilden, R n and R 12 with the nitrogen atom to which they are bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-ring monocyclic or bicyclic ring,
R13 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C3-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)- Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkoxy- (Ci-C7)-alkoxy-(Ci-C7)-alkyl, Aryl, Aryl-(Ci-C7)-alkyl, Aiyl-(Ci-C7)-alkoxy-(Ci-C7)- alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (C1-O7)- Alkyl-aminocarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl-aminocarbonyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]amino-(C2-C5)-alkyl, (Ci-C7)-Alkyl-amino-(C2-C5)-alkyl, Aryl-(Ci- C7)-alkyl-amino-(C2-C5)-alkyl, R14S-(Ci-C7)-alkyl, R14(0)S-(Ci-C7)-alkyl, R1402S- (Ci-C7)-alkyl, Hydroxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)- alkyl, Tris-[(Ci-C7)-Alkyl]silyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-Alkyl](aryl)silyl(Ci-C7)- alkyl, [(Ci-C7)-Alkyl]-bis-(aryl)silyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyloxy-(Ci-C7)- alkyl, (C3-C7)-Cycloalkylcarbonyloxy-(Ci-C7)-alkyl, Arylcarbonyloxy-(Ci-C7)-alkyl, Heteroarylcarbonyloxy-(Ci-C7)-alkyl, Heterocyclylcarbonyloxy-(Ci-C7)-alkyl, Aryloxy- (Ci-C7)-alkyl, Heteroaryloxy-(Ci-C7)-alkyl, , (Ci-C7)-Alkoxycarbonyl steht, R14 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C3-C7)-Haloalkinyl, (C3-Ci0)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (G-C7)- Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]amino, (G-G)- Alkyl-amino, Aryl-(Ci-C7)-amino, Aryl-(Ci-C4)-alkyl-amino, Aryl-[(G-G)- alkyl]amino; (C3-C7)-Cycloalkyl-amino, (C3-C7)-Cycloalkyl-[(Ci-C7)-alkyl]amino; N- Azetidinyl, N-Pyrrolidinyl, N-Piperidinyl. N-Morpholinyl, steht R 13 for hydrogen, (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4- Cio) -Halocycloalkenyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) - alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkoxy- ( Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, aryl, aryl- (Ci-C 7 ) -alkyl, Aiyl- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) - alkyl, Heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (Ci-C 7 ) -alkyl, (C4-C10) -cycloalkenyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] aminocarbonyl- (Ci-C 7 ) -alkyl, (C1-O7) - alkyl-aminocarbonyl- (Ci-C 7 ) -alkyl, aryl- (Ci-C 7 ) - alkyl-aminocarbonyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] amino- (C 2 -C 5 ) -alkyl, (Ci-C 7 ) -alkyl-amino- (C 2 -C 5 ) -alkyl, aryl- (Ci- C 7 ) -alkyl-amino- (C 2 -C 5 ) -alkyl, R 14 S- (Ci-C 7 ) -alkyl, R 14 (0) S - (Ci-C 7 ) -alkyl, R 14 0 2 S- (Ci-C 7 ) -alkyl, hydroxycarbonyl- (Ci-C 7 ) -alkyl, heterocyclyl, heterocyclyl- (Ci-C 7 ) -alkyl, tris - [(Ci-C 7 ) -alkyl] silyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] (aryl) silyl (Ci-C 7 ) -alkyl, [(Ci -C 7 ) -alkyl] -bis- (aryl) silyl- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkylcarbonyloxy- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) - Cycloalkylcarbonyloxy- (Ci-C 7 ) -alkyl, arylcarbonyloxy- (Ci-C 7 ) -alkyl, heteroarylcarbonyloxy- (Ci-C 7 ) -alkyl, heterocyclylcarbonyloxy- (Ci-C 7 ) -alkyl, aryloxy- (Ci-C 7 ) -alkyl, heteroaryloxy- (Ci-C 7 ) -alkyl,, (Ci-C 7 ) -alkoxycarbonyl, R 14 for hydrogen, (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (Ci-C 7 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 3 -C 7 ) -haloalkynyl, (C 3 -Ci 0 ) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4 -Cio) -halocycloalkenyl, (GC 7 ) - alkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, heterocyclyl- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (Ci-C 7 ) -alkyl, (C 4 - Cio) -Cycloalkenyl- (Ci-C 7 ) -alkyl, bis - [(Ci-C 7 ) -alkyl] amino, (GG) -alkyl-amino, aryl- (Ci-C 7 ) -amino, aryl- ( Ci-C4) -alkyl-amino, aryl - [(GG) - alkyl] amino; (C 3 -C 7 ) -cycloalkyl-amino, (C 3 -C 7 ) -cycloalkyl - [(Ci-C 7 ) -alkyl] amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl. N-morpholinyl
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen. X and Y independently represent O (oxygen) or S (sulfur).
3. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 3. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, (CrG,)-Alkoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (CrG,) - alkoxy,
R3 für Wasserstoff, Halogen, (CrG,)-Alkoxy steht, R 3 represents hydrogen, halogen, (CrG,) - alkoxy,
R4 für Halogen, Cyano, N02, C(0)NH2, C(S)NH2, (G-G)-Haloalkyl, (G-G)-Alkinyl steht, R 4 represents halogen, cyano, N0 2 , C (0) NH 2 , C (S) NH 2 , (GG) -haloalkyl, (GG) -alkynyl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, (G-G)-Alkyl. R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (GG) -alkyl.
(G-G)-Haloalkyl, (G-G)-Alkoxy, (G-G)-Haloalkoxy stehen, (G-G) -haloalkyl, (G-G) -alkoxy, (G-G) -haloalkoxy,
G für unverzweigtes oder verzweigtes (G-G)-Alkylen steht, G stands for unbranched or branched (G-G) -alkylene,
Q für einen Rest der Formel
Figure imgf000162_0001
steht, R8 für Wasserstoff, (G-C6)-Alkyl, (G-C6)-Haloalkyl, Aryl, Aiyl-(Ci-C6)-alkyl, Q for a remainder of the formula
Figure imgf000162_0001
stands, R 8 for hydrogen, (GC 6 ) -alkyl, (GC 6 ) -haloalkyl, aryl, Aiyl- (Ci-C 6 ) -alkyl,
Heteroaryl, (C2-C6)-Alkinyl, (C2-C6)-Alkenyl, C(0)R13, C(0)0R13, (G-C6)-Alkoxy- (Ci-Cö)-alkyl steht, Heteroaryl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkenyl, C (0) R 13 , C (0) 0R 13 , (GC 6 ) -alkoxy- (Ci-C ö ) - alkyl stands,
R9 für Wasserstoff oder (Ci-C- -Alkyl steht, R 9 represents hydrogen or (Ci-C- alkyl,
R10 für Cyano, NO2, Heteroaryl, Heteroaryl-(Ci-Ce)-alkyl, Heterocyclyl, Heterocyclyl-R 10 for cyano, NO2, heteroaryl, heteroaryl (Ci-Ce) alkyl, heterocyclyl, heterocyclyl
(Ci-C6)-alkyl, RnR12N-(Ci-C6)-alkyl, R130-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, (G-C6)- Alkylcarbonyloxy-(Ci-C6)-alkyl, (C3-C6)-Cycloalkylcarbonyloxy-(G-C6)-alkyl, Arylcarbonyloxy-(Ci-C6)-alkyl, Heteroarylcarbonyloxy-(G-C6)-alkyl, (Ci-C 6 ) -alkyl, R n R 12 N- (Ci-C 6 ) -alkyl, R 13 0- (Ci-C 6 ) -alkyl, cyano- (Ci-C 6 ) -alkyl, (GC 6 ) - Alkylcarbonyloxy- (Ci-C 6 ) -alkyl, (C3-C6) -cycloalkylcarbonyloxy- (G-C6) -alkyl, arylcarbonyloxy- (Ci-C 6 ) -alkyl, heteroarylcarbonyloxy- (GC 6 ) -alkyl,
Heterocyclylcarbonyloxy-(Ci-C6)-alkyl, OR13, NRnR12, SR14, S(0)R14, S02R14, R14S- (Ci-Cö)-alkyl, R14(0)S-(G-C6)-alkyl, R1402S-(G-C6)-alkyl, Tris-[(G-C6)-Alkyl]silyl- (Ci-C6)-alkyl, Bis-[(Ci-C6)-Alkyl](aryl)silyl(Ci-C6)-alkyl, [(G-C6)-Alkyl]-bis- (aryl)silyl-(Ci-Ce)-alkyl, Tris-[(G-C6)-Alkyl]silyl, Bis-hydroxyboiyl-(C|-C(,)-alkyl. Bis- |(C |-C(,)-alkoxy |boiyl-(C|-C ,)-alkyl. Tetramethyl- 1, 3, 2-Dioxaborolan-2-yl, Heterocyclylcarbonyloxy- (Ci-C 6 ) -alkyl, OR 13 , NR n R 12 , SR 14 , S (0) R 14 , S0 2 R 14 , R 14 S- (Ci-C ö ) -alkyl, R 14 ( 0) S- (GC 6 ) -alkyl, R 14 0 2 S- (GC 6 ) -alkyl, tris - [(GC 6 ) -alkyl] silyl- (Ci-C 6 ) -alkyl, bis - [(Ci -C 6 ) -alkyl] (aryl) silyl (Ci-C 6 ) -alkyl, [(GC 6 ) -alkyl] -bis- (aryl) silyl- (Ci-Ce) -alkyl, tris - [(GC 6 ) -Alkyl] silyl, bis-hydroxyboiyl- (C | -C ( ,) - alkyl. Bis- | (C | -C ( ,) - alkoxy | boiyl- (C | -C,) - alkyl. Tetramethyl-1 , 3, 2-dioxaborolan-2-yl,
Tetramethyl-l,3,2-Dioxaborolan-2-yl-(Ci-C6)-alkyl, Nitro-(C |-C(,)-alkyl. , C(0)R13, , Bis-(Ci-C6)-alkoxymethyl, Bis-(Ci-C6)-alkoxymethyl-(Ci-C6)-alkyl steht, Tetramethyl-1,3,2-Dioxaborolan-2-yl- (Ci-C 6 ) -alkyl, nitro- (C | -C ( ,) - alkyl., C (0) R 13 ,, bis- (Ci- C 6 ) alkoxymethyl, bis (Ci-C 6 ) alkoxymethyl (Ci-C 6 ) alkyl,
R8 und R10 mit dem Kohlenstoffatom, an das sie gebunden sind, ein vollständig gesättigtes oder teilgesättigtes, und gegebenenfalls weiter substituiertes 3 bis 10-gliedriges R 8 and R 10, with the carbon atom to which they are bonded, are a fully saturated or partially saturated, and optionally further substituted 3 to 10-membered one
monocyclisches oder bicyclisches Heterocyclyl bilden, form monocyclic or bicyclic heterocyclyl,
R11 und R12 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (CrG,)- Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C6)-Haloalkenyl, (Cs-CeJ-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-Ce)-Alkoxy- (Ci-Cö)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl- (Ci-Ce)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, COR13, S02R14, Heterocyclyl, (Ci-Ce)- Alkoxycarbonyl, Bis-[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkyl- aminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl-aminocarbonyl-(Ci-C6)-alkyl, Aryl- (Ci-C6)-alkoxycarbonyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl, (C2-G,)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C6)-alkyl stehen, oder R11 und R12 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 11 and R 12 are identical or different and, independently of one another, represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl , (Ci-Cio) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (Cs-CeJ-haloalkynyl, (C 3 -Cio) -cycloalkyl, (C3-C10) -halocycloalkyl, (C4-Cio) -cycloalkenyl , (C4-Cio) -Halocycloalkenyl, (Ci-Ce) -Alkoxy- (Ci-C ö ) -alkyl, (Ci-C 6 ) -haloalkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -Alkylthio- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -haloalkylthio- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -haloalkyl, aryl, Aryl- (Ci-Ce) -alkyl, heteroaryl, heteroaryl- (Ci-C 6 ) -alkyl, (C3-C6) -cycloalkyl- (Ci-C6) -alkyl, (C 4 -Cio) -cycloalkenyl- (Ci -C 6 ) alkyl, COR 13 , S0 2 R 14 , heterocyclyl, (Ci-Ce) - alkoxycarbonyl, bis - [(Ci-C 6 ) alkyl] aminocarbonyl (Ci-C 6 ) alkyl, (Ci -Ce) -Alkyl- aminocarbonyl- (Ci-C 6 ) -alkyl, aryl- (Ci-C 6 ) -alkyl-aminocarbonyl- (Ci-C 6 ) -alkyl, aryl- (Ci-C 6 ) -alkoxycarbonyl, Heteroaryl- (Ci-C 6 ) -alkoxycarbonyl, (C 2 -G,) -alkenyloxycarbonyl, (C 2 -C 6 ) -alkinyloxycarbonyl , Heterocyclyl- (Ci-C 6 ) -alkyl, or R 11 and R 12 with the nitrogen atom to which they are attached form a completely saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, optionally interrupted by heteroatoms and optionally further substituted,
R13 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (CYG,)-Haloalkenyl. (C3-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-Ce)- Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkoxy-(C |-C ,)-alkoxy-(C|-C(,)-alkyl. (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkoxy- (Ci-C6)-alkoxy-(Ci-C6)-alkyl, Aryl, Aryl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxy-(Ci-C6)- alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (C|-C(,)- Alkyl-aminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkyl-aminocarbonyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]amino-(C2-C4)-alkyl, (Ci-C6)-Alkyl-amino-(C2-C4)-alkyl, Aryl-(Ci- C6)-alkyl-amino-(C2-C4)-alkyl, R14S-(Ci-C6)-alkyl, R14(0)S-(Ci-C6)-alkyl, R1402S- (Ci-Ce)-alkyl, Hydroxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)- alkyl, Tris-[(Ci-C6)-Alkyl]silyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)-Alkyl](aryl)silyl(Ci-C6)- alkyl, [(Ci-C6)-Alkyl]-bis-(aryl)silyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyloxy-(Ci-C6)- alkyl, (C3-C6)-Cycloalkylcarbonyloxy-(Ci-C6)-alkyl, Arylcarbonyloxy-(Ci-Cö)-alkyl, Heteroarylcarbonyloxy-(Ci-C6)-alkyl, Heterocyclylcarbonyloxy-(Ci-C6)-alkyl, Aryloxy- (Ci-Ce)-alkyl, Heteroaryloxy-(Ci-C6)-alkyl, , (C 1 -C(,)-Alkoxycarbonyl steht, R 13 for hydrogen, (Ci-C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C 6 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (CYG,) - haloalkenyl. (C3-C6) -haloalkynyl, (C3-Cio) -cycloalkyl, (C3-Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4-Cio) -halocycloalkenyl, (Ci-Ce) -alkoxy- (Ci -C 6 ) -alkyl, (Ci-C 6 ) -haloalkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) - haloalkyl, (Ci-C 6 ) - Alkoxy- (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkoxy- (C | -C,) -alkoxy- (C | -C ( ,) - alkyl. (Ci-C 6 ) -Alkoxy- (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 6 ) -alkyl, (C3-C6) cycloalkyl (Ci-C6) alkyl, (C4-C10) - (6 Ci-C) alkyl cycloalkenyl, - bis [(Ci-C6) alkyl] aminocarbonyl (Ci C 6 ) -alkyl, (C | -C ( ,) -alkyl-aminocarbonyl- (Ci-C 6 ) -alkyl, aryl- (Ci-C 6 ) -alkyl-aminocarbonyl- (Ci-C 6 ) -alkyl, bis - [(Ci-C6) alkyl] amino- (C 2 -C 4) alkyl, (Ci-C6) alkyl-amino- (C 2 -C 4) alkyl, aryl (Ci- C 6) - alkyl-amino- (C 2 -C 4 ) -alkyl, R 14 S- (Ci-C 6 ) -alkyl, R 14 (0) S- (Ci-C 6 ) -alkyl, R 14 0 2 S- ( Ci-Ce) alkyl, hydroxycarbonyl (Ci-C 6 ) -alkyl, heterocyclyl, heterocyclyl- (Ci-C 6 ) - alkyl, tris - [(Ci-C 6 ) -alkyl] silyl- (Ci-C 6 ) -alkyl, bis - [(Ci-C 6 ) -Alkyl] (aryl) silyl (Ci-C 6 ) -alkyl, [(Ci-C 6 ) -alkyl] -bis- (aryl) silyl- (Ci-C 6 ) -alkyl, (Ci-C 6 ) - alkyl alkyl, (C3-C6) -Cycloalkylcarbonyloxy- (Ci-C6) alkyl, arylcarbonyloxy (Ci-C ö) alkyl, Heteroarylcarbonyloxy- (Ci-C 6), heterocyclylcarbonyloxy - alkylcarbonyloxy (Ci-C 6) - (Ci-C 6 ) -alkyl, aryloxy- (Ci-Ce) -alkyl, heteroaryloxy- (Ci-C 6 ) -alkyl,, (C 1 -C ( ,) - alkoxycarbonyl,
R14 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkmyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C(,)-Haloalkcnyl. (C3-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-G,)- Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aiyl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-Cö)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]amino, (Ci-Ce)- Alkyl-amino, Aryl-(Ci-C6)-amino, Aryl-(Ci-C2)-alkyl-amino, Aryl-[(Ci-Ce)- alkyl]amino; (C3-C6)-Cycloalkyl-amino, (C3-C6)-Cycloalkyl-[(Ci-C6)-alkyl]amino; N- Azetidinyl, N-Pyrrolidinyl, N-Piperidinyl. N-Morpholinyl, steht und R 14 for hydrogen, (Ci-C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -Alkmyl, (Ci-C 6 ) -cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C ( ,) - Haloalknyl. (C3-C6) -haloalkynyl, (C3-Cio) -cycloalkyl, (C3-Cio) -halocycloalkyl, (C4-Cio) -cycloalkenyl, (C4-Cio) - Halocycloalkenyl, (Ci-G,) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -haloalkyl, aryl, Aiyl- (Ci-C 6 ) -alkyl , heteroaryl, heteroaryl (Ci-C 6) alkyl, (Ci-C 6) alkyl heterocyclyl, (C3-C6) cycloalkyl (Ci-C ö) alkyl, (C 4 -Cio) -cycloalkenyl - (Ci-C 6 ) -alkyl, bis - [(Ci-C 6 ) -alkyl] amino, (Ci-Ce) -alkyl-amino, aryl- (Ci-C 6 ) -amino, aryl- (Ci- C 2 ) -alkyl-amino, aryl - [(Ci-Ce) -alkyl] amino; (C3-C6) -cycloalkyl-amino, (C3-C6) -cycloalkyl- [(Ci-C6) -alkyl] amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, and
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen. X and Y independently represent O (oxygen) or S (sulfur).
4. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 4. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, Methoxy, Ethoxy, Prop-l-yloxy, But-l-yloxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-l-yloxy, but-l-yloxy,
R3 für Wasserstoff, Fluor, Chlor, Brom, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1-Dimethyleth-l-yloxy steht, R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-l-yloxy, prop-2-yloxy, but-l-yloxy, but-2-yloxy, 2-methylprop-l-yloxy, 1,1 -Dimethyleth-l-yloxy stands,
R4 für Fluor, Chlor, Brom, Cyano, NO2, C(0)NH2, C(S)NH2, Trifluormethyl, R 4 for fluorine, chlorine, bromine, cyano, NO2, C (0) NH 2 , C (S) NH2, trifluoromethyl,
Difluormethyl, Pentafluorethyl, Ethinyl, Propin- 1-yl, 1 -Butin- 1-yl, Pentin-l-yl, Hexin- 1- yl steht, Difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano,
Methyl, Ethyl, Prop-l-yl, 1-Methylethyl, But-l-yl, 1 -Methylpropyl, 2-Methylpropyl, 1,1-Dimethylethyl, n-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1,1- Dimethylpropyl, 1,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1-Ethylpropyl, n-Hexyl, 1- Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1,2- Dimethylbutyl, 1,3-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3- Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2- Trimethylpropyl, 1 -Ethyl- 1-methylpropyl, l-Ethyl-2-methylpropyl, Trifluormethyl, Difluormethyl, Pentafluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1- Dimethyleth-l-yloxy, Difluormethoxy, Trifluormethoxy, Pentafluorethoxy, 2,2- Difluorethoxy, 2,2,2-Trifluorethoxy stehen, Methyl, ethyl, prop-l-yl, 1-methylethyl, but-l-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2, 2- trimethylpropyl, 1-ethyl-1-methylpropyl, l-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-l-yloxy, Prop-2-yloxy, but-l-yloxy, but-2-yloxy, 2-methylprop-l-yloxy, 1,1-dimethyleth-l-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy stand,
G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Prop-l-yl)methylen, (Prop-2- yl)methylen, (But-l-yl)methylen, (But-2-yl)methylen, (Pent-l-yl)methylen, (Pent-2- yl)methylen, (Pent-3-yl)methylen, (Dimethyl)methylen, (Diethyl)methylen, Ethylen, n- Propylen, (l-Methyl)ethyl-l-en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1-en, 2-Methylpropyl- 1-en, 3 -Methylpropyl- 1-en, 1,1-Dimethylethyl- 1-en, 2,2-Dimethylethyl- 1-en, 1-Ethylethyl-l-en, 2-Ethylethyl-l-en, l-(Prop-l-yl)ethyl-l-en, 2-(Prop-l-yl)ethyl- 1-en, l-(Prop-2-yl)ethyl-l-en, 2-(Prop-2-yl)ethyl-l-en, 1,1,2-Trimethylethyl-l-en, 1,2,2- Trimethylethyl-l-en, 1,1,2,2-Tetramethylethyl-l-en, n-Pentylen, 1-Methylbutyl- 1-en, 2- Methylbutyl- 1 -en, 3 -Methylbutyl- 1 -en, 4-Methylbutyl- 1 -en, 1 , 1 -Dimethylpropyl- 1 -en, G for methylene, (methyl) methylene, (ethyl) methylene, (prop-l-yl) methylene, (prop-2- yl) methylene, (but-l-yl) methylene, (but-2-yl) methylene, (Pent-l-yl) methylene, (pent-2-yl) methylene, (pent-3-yl) methylene, (dimethyl) methylene, (diethyl) methylene, ethylene, n-propylene, (l-methyl) ethyl 1-ene, (2-methyl) ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1 -en, 2,2-dimethylethyl-1-en, 1-ethylethyl-l-ene, 2-ethylethyl-l-ene, 1- (prop-l-yl) ethyl-l-ene, 2- (prop-l -yl) ethyl-1-ene, 1- (prop-2-yl) ethyl-1-ene, 2- (prop-2-yl) ethyl-1-ene, 1,1,2-trimethylethyl-1-ene , 1,2,2-trimethylethyl-1-ene, 1,1,2,2-tetramethylethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl - 1 -en, 4-methylbutyl-1-en, 1, 1-dimethylpropyl-1-en,
2.2-Dimethylpropyl-l-en, 3,3-Dimethylpropyl-l-en, 1,2-Dimethylpropyl-l-en, 1,3- Dimethylpropyl-l-en, 1-Ethylpropyl-l-en, n-Hexylen, 1-Methylpentyl-l-en, 2- Methylpentyl-l-en, 3-Methylpentyl-l-en, 4-Methylpentyl-l-en, 1,1-Dimethylbutyl-l-en,2.2-dimethylpropyl-1-en, 3,3-dimethylpropyl-1-en, 1,2-dimethylpropyl-1-en, 1,3-dimethylpropyl-1-en, 1-ethylpropyl-1-en, n-hexylene, 1-methylpentyl-l-ene, 2-methylpentyl-l-ene, 3-methylpentyl-l-ene, 4-methylpentyl-l-ene, 1,1-dimethylbutyl-l-ene,
1.2-Dimethylbutyl-l-en, 1,3-Di-methylbutyl-l-en, 2,2-Dimethylbutyl-l-en, 2,3- Dimethylbutyl-l-en, 3,3-Dimethylbutyl-l-en, 1-Ethylbutyl-l-en, 2-Ethylbutyl-l-en,1,2-dimethylbutyl-l-ene, 1,3-dimethylbutyl-l-ene, 2,2-dimethylbutyl-l-ene, 2,3-dimethylbutyl-l-ene, 3,3-dimethylbutyl-l-ene, 1-ethylbutyl-l-ene, 2-ethylbutyl-l-ene,
1.1.2-Trimethylpropyl- 1 -en, 1 ,2,2-Trimethylpropyl- 1 -en, 1 -Ethyl- 1 -methylpropyl- 1 -en,1.1.2-trimethylpropyl-1-ene, 1, 2,2-trimethylpropyl-1-ene, 1-ethyl-1-methylpropyl-1-ene,
1 -Ethyl-2-methylpropyl- 1 -en steht, 1-ethyl-2-methylpropyl-1-ene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen und X and Y independently of one another represent O (oxygen) or S (sulfur) and
Q für eine der nachfolgend spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q- 57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q- 180, Q-182 bis Q-185, Q-193 bis Q-195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bisQ for one of the following specifically named groupings Ql to Q-54, Q-56 to Q- 57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q-141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q-195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to
Q-440 steht: Q-440 says:
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5. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 5. Compounds of general formula (I) according to Claim 1 and / or their salt, characterized in that
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Wasserstoff, Fluor, Chlor, Brom, Methoxy steht, R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy,
R4 für Fluor, Chlor, Brom, Cyano, NO2, C(0)NH2, C(S)NH2, Trifluormethyl, Ethinyl, Propin- 1-yl steht, R 4 represents fluorine, chlorine, bromine, cyano, NO 2 , C (0) NH 2 , C (S) NH 2 , trifluoromethyl, ethynyl, propyn-1-yl,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy stehen, G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Dimethyl)methylen, Ethylen, n-R 5 , R 6 and R 7 independently represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, G for methylene, (methyl) methylene, (ethyl) methylene, (dimethyl) methylene, ethylene, n-
Propylen, (l-Methyl)ethyl-l-en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1-en, 2-Methylpropyl-l-en, 3 -Methylpropyl- 1-en, 1, 1-Dimethylethyl-l-en, 2,2-Dimethylethyl- 1-en, 1-Ethylethyl-l-en, 2-Ethylethyl-l-en, l-(Prop-l-yl)ethyl-l-en, 2-(Prop-l-yl)ethyl-Propylene, (l-methyl) ethyl-l-ene, (2-methyl) ethyl-l-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-l-ene, 3-methylpropyl- 1- en, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1- (prop-1-yl) ethyl-1 -en, 2- (prop-l-yl) ethyl-
1-en, l-(Prop-2-yl)ethyl-l-en, 2-(Prop-2-yl)ethyl-l-en, n-Pentylen, 1-Methylbutyl-l-en,1-en, l- (prop-2-yl) ethyl-l-en, 2- (prop-2-yl) ethyl-l-en, n-pentylene, 1-methylbutyl-l-en,
2-Methylbutyl- 1 -en, 3 -Methylbutyl- 1 -en, 4-Methylbutyl- 1 -en, 1 , 1 -Dimethylpropyl- 1 -en, 2,2-Dimethylpropyl-l-en, 3, 3 -Dimethylpropyl- 1-en, 1,2-Dimethylpropyl-l-en, 1,3- Dimethylpropyl-l-en, 1-Ethylpropyl-l-en, n-Hexylen, steht, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl- 1-en, 1,2-dimethylpropyl-1-en, 1,3-dimethylpropyl-1-en, 1-ethylpropyl-1-en, n-hexylene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen X and Y independently represent O (oxygen) or S (sulfur)
Q für eine der in Anspruch 4 spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q-57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q- 180, Q-182 bis Q-185, Q-193 bis Q-195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bis Q-440 steht. Q for one of the groupings specifically mentioned in claim 4 Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q- 141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q-195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q-440 stands.
6. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 6. Compounds of general formula (I) according to claim 1 and / or their salt, characterized in that
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Fluor steht, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2, C(0)NH2, C(S)NH2 steht, R 4 represents chlorine, bromine, cyano, NO2, C (0) NH 2 , C (S) NH2,
R5, R6 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Trifluormethyl, Methoxy, Trifluormethoxy stehen, R 5 , R 6 and R 7 independently represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Dimethyl)methylen, Ethylen, n- Propylen, (l-Methyl)ethyl-l-en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1-en, 2- Methylpropyl-l-en, 3 -Methylpropyl- 1-en, n-Pentylen, n-Hexylen steht, G for methylene, (methyl) methylene, (ethyl) methylene, (dimethyl) methylene, ethylene, n-propylene, (1-methyl) ethyl-1-ene, (2-methyl) ethyl-1-ene, n-butylene , 1-methylpropyl-1-en, 2- methylpropyl-1-en, 3-methylpropyl-1-en, n-pentylene, n-hexylene,
X und Y unabhängig voneinander für O (Sauerstoff) oder S (Schwefel) stehen und X and Y independently represent O (oxygen) or S (sulfur) and
Q für eine der in Anspruch 4 spezifisch genannten Gruppierungen Q-l bis Q-54, Q-56 bis Q-57, Q-60 bis Q-89, Q-91 bis Q-129, Q-131 bis Q-139, Q-141 bis Q-144, Q-146 bis Q- 180, Q-182 bis Q-185, Q-193 bis Q-195, Q-200 bis Q-208, Q-210 bis Q-370, Q-395 bis Q-440 steht. Q for one of the groupings specifically mentioned in claim 4 Ql to Q-54, Q-56 to Q-57, Q-60 to Q-89, Q-91 to Q-129, Q-131 to Q-139, Q- 141 to Q-144, Q-146 to Q-180, Q-182 to Q-185, Q-193 to Q-195, Q-200 to Q-208, Q-210 to Q-370, Q-395 to Q-440 stands.
7. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 7. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Fluor steht, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2 steht, R 4 stands for chlorine, bromine, cyano, NO2,
R5 für Wasserstoff steht, R 5 represents hydrogen,
R6 für Wasserstoff, Fluor steht, R 6 represents hydrogen, fluorine,
R7 für Wasserstoff steht, R 7 represents hydrogen,
G für Methylen steht, G stands for methylene,
X für O (Sauerstoff) oder S (Schwefel) steht, X stands for O (oxygen) or S (sulfur),
Y für O (Sauerstoff) steht, und Y stands for O (oxygen), and
Q für eine der in Anspruch 4 spezifisch genannten Gruppierungen Q-l bis Q-35, Q-41, Q- 42, Q-71 bis Q-80, Q-l 15, Q-120, Q-152 bis Q-155, Q-166 bis Q-170, Q-176 bis Q-206, Q-211 bis Q-214, Q-280 bis Q-358, Q-362 bis Q-370, Q-405, Q-408 bis Q-410, Q-421 bis Q-429 steht. Q for one of the groupings Ql to Q-35, Q-41, Q- 42, Q-71 to Q-80, Ql 15, Q-120, Q-152 to Q-155, Q-166 to Q-170, Q-176 to Q-206, Q-211 to Q-214, Q-280 to Q-358, Q-362 to Q-370, Q-405, Q-408 to Q-410, Q -421 to Q-429.
8. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salz, dadurch gekennzeichnet, dass 8. Compounds of general formula (I) according to Claim 1 and / or their salt, characterized in that
R1 für Wasserstoff steht, R 1 represents hydrogen,
R2 für Fluor steht, R 2 represents fluorine,
R3 für Fluor steht, R 3 stands for fluorine,
R4 für Chlor, Brom, Cyano, NO2 steht, R 4 stands for chlorine, bromine, cyano, NO2,
R5 für Wasserstoff steht, R 5 represents hydrogen,
R6 für Wasserstoff, Fluor steht, R 6 represents hydrogen, fluorine,
R7 für Wasserstoff steht, R 7 represents hydrogen,
G für Methylen steht, G stands for methylene,
X für O (Sauerstoff) oder S (Schwefel) steht, X stands for O (oxygen) or S (sulfur),
Y für O (Sauerstoff) steht, und Y stands for O (oxygen), and
Q für eine der in Anspruch 4 spezifisch genannten Gruppierungen Q-l, Q-2, Q-6, Q-23, Q- 26, Q-31, Q-41, Q-71, Q-72, Q-l 15, Q-154, Q-166, Q-176, Q-201, Q-211, Q-280, Q- 286, Q-288, Q-301, Q-350, Q-366, Q-367, Q-368, Q-405, Q-421, Q-422, Q-424 steht. Q for one of the groupings Ql, Q-2, Q-6, Q-23, Q-26, Q-31, Q-41, Q-71, Q-72, Q-15, Q-154 , Q-166, Q-176, Q-201, Q-211, Q-280, Q-286, Q-288, Q-301, Q-350, Q-366, Q-367, Q-368, Q -405, Q-421, Q-422, Q-424.
9. Verwendung einer oder mehrere Verbindungen der allgemeinen Formel (I) wie in einem der Ansprüche 1 bis 8 definiert und/oder deren Salze, als Herbizid und/oder 9. Use of one or more compounds of the general formula (I) as defined in one of claims 1 to 8 and / or their salts, as a herbicide and / or
Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen. Plant growth regulator, preferably in crops of useful and / or ornamental plants.
10. Herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel eine oder mehrere Verbindungen der allgemeinen Formel (I) wie in einem der Ansprüche 1 bis 8 definiert und/oder deren Salze enthält, und ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii), mit 10. Herbicidal and / or plant growth-regulating agent, characterized in that the agent has one or more compounds of the general formula (I) as in one of the claims 1 to 8 defined and / or contains their salts, and one or more other substances selected from groups (i) and / or (ii), with
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and / or further growth regulators,
(ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. (ii) one or more formulation auxiliaries customary in crop protection.
11. Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge 11. A method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount
- einer oder mehrerer Verbindungen der allgemeinen Formel (I), wie in einem der - One or more compounds of the general formula (I), as in one of the
Ansprüche 1 bis 8 definiert und/oder deren Salze, oder Claims 1 to 8 defined and / or their salts, or
eines Mittels nach Anspruch 10, an agent according to claim 10,
auf die Pflanzen, Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert wird. on the plants, plant seeds, the soil in which or on which the plants grow, or the area under cultivation.
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